Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 6564-72-3 | MDL No. : | MFCD00023849 |
Formula : | C34H36O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OGOMAWHSXRDAKZ-RUOAZZEASA-N |
M.W : | 540.65 | Pubchem ID : | 11731256 |
Synonyms : |
|
Num. heavy atoms : | 40 |
Num. arom. heavy atoms : | 24 |
Fraction Csp3 : | 0.29 |
Num. rotatable bonds : | 13 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 152.6 |
TPSA : | 66.38 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.06 cm/s |
Log Po/w (iLOGP) : | 4.61 |
Log Po/w (XLOGP3) : | 4.98 |
Log Po/w (WLOGP) : | 5.07 |
Log Po/w (MLOGP) : | 2.86 |
Log Po/w (SILICOS-IT) : | 5.62 |
Consensus Log Po/w : | 4.63 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.92 |
Solubility : | 0.000657 mg/ml ; 0.00000122 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -6.11 |
Solubility : | 0.000417 mg/ml ; 0.000000771 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -10.11 |
Solubility : | 0.0000000422 mg/ml ; 0.0000000001 mol/l |
Class : | Insoluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 5.59 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333 h; Molecular sieve Stage #2: at 20℃; for 2 h; |
EXAMPLE XXI 2,3,4,6-Tetra-O-benzyl-D-glucopyranone 4 g freshly activated molecular sieve 4 Å and 3.3 g N-methylmorpholine-N-oxide are added to a solution of 10.0 g 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in 140 ml dichloromethane. The solution is stirred for 20 min at ambient temperature, before adding 0.3 g of tetrapropylammonium perruthenate. After 2 h stirring at ambient temperature the solution is diluted with dichloromethane and filtered through Celite. The filtrate is washed with aqueous sodium thiosulfate solution and water and then dried over sodium sulfate. After the solvent is removed the residue is chromatographed through silica gel (cyclohexane/ethyl acetate 4:1). Yield: 8.2 g (82percent of theory) Mass spectrum (ESI+): m/z=539 [M+H]+ |
82% | Stage #1: With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333 h; Molecular sieve Stage #2: With tetrapropylammonium perruthennate In dichloromethane at 20℃; for 2 h; Molecular sieve |
EXAMPLE V 2,3,4,6-Tetra-O-benzyl-D-glucopyranone To a solution of 10.0 g 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in 140 mL dichloromethane are added 4 g freshly activated molecular sieves 4 Å and 3.3 g N-methylmorpholine-N-oxide. The solution is stirred for 20 min at ambient temperature, before 0.3 g tetra-n-propylammonium perruthenate are added. After 2 h stirring at ambient temperature the solution is diluted with dichloromethane and filtered through Celite. The filtrate is washed with aqueous sodium thiosulfate solution and water and then dried over sodium sulfate. After the solvent is evaporated, the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1). Yield: 8.2 g (82percent of theory) Mass spectrum (ESI+): m/z=539 [M+H]+ |
82% | Stage #1: With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333 h; Molecular sieve 4A Stage #2: at 20℃; for 2 h; |
To a solution of 10.0 g 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in 140 mL dichloromethane are added 4 g freshly activated molecular sieves 4 Å and 3.3 g N-methylmorpholine-N-oxide. The solution is stirred for 20 min at ambient temperature, before 0.3 g tetra-n-propylammonium perruthenate are added. After 2 h stirring at ambient temperature the solution is diluted with dichloromethane and filtered through Celite. The filtrate is washed with aqueous sodium thiosulfate solution and water and then dried over sodium sulfate. After the solvent is evaporated, the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1). Yield: 8.2 g (82percent of theory) Mass spectrum (ESI+): m/z=539 [M+H]+ |
82% | Stage #1: With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333 h; Molecular sieve Stage #2: With tetrapropylammonium perruthennate In dichloromethane at 20℃; for 2 h; |
4 g freshly activated molecular sieve 4 Å and 3.3 g N-methylmorpholine-N-oxide are added to a solution of 10.0 g 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in 140 ml dichloromethane. The solution is stirred for 20 min at ambient temperature, before adding 0.3 g of tetrapropylammonium perruthenate. After 2 h stirring at ambient temperature the solution is diluted with dichloromethane and filtered through Celite. The filtrate is washed with aqueous sodium thiosulphate solution and water and then dried over sodium sulphate. After the solvent has been eliminated the residue is chromatographed through silica gel (cyclohexane/ethyl acetate 4:1). Yield: 8.2 g (82percent of theory) Mass spectrum (ESI+): m/z=539 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With lithium aluminium tetrahydride In tetrahydrofuran Ambient temperature; | |
With lithium aluminium tetrahydride In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 16% 2: 60% | With silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride In dichloromethane 1.) -40-0 deg C, 40 min, 2.) 0 deg C, 3 h; | |
1: 33% 2: 28% | With hydrogen bromide; cobalt(II) bromide In dichloromethane at 25℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With triethylamine In benzene for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With 2-methoxyacetic acid; ytterbium(III) triflate In 1,2-dichloro-ethane at 53℃; for 36h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N,N-dimethyl acetamide; silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride In dichloromethane at -40℃; 5.0 equiv. of N,N-dimethylacetamide; Yield given. Yields of byproduct given; | ||
With trimethylsilyl bromide; 4 A molecular sieve; tetrabutylammomium bromide; cobalt(II) bromide In dichloromethane for 16h; Ambient temperature; Yield given. Yields of byproduct given; | ||
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 4.5h; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With 4 A molecular sieve; 2-methoxyacetic acid; ytterbium(III) triflate In dichloromethane for 4h; Heating; | |
88% | With N,N-dimethyl acetamide; silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride In dichloromethane 1.) -40 deg C, 2.) -40 -> 0 deg C, 1 h, 3.) 0 deg C, 18 h; | |
69% | With trimethylsilyl bromide; 4 A molecular sieve; tetrabutylammomium bromide; cobalt(II) bromide In dichloromethane at 22 - 28℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 51% 2: 31% | With N,N-dimethyl acetamide; silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride In dichloromethane at -40℃; 5.0 equiv. of N,N-dimethylacetamide; | |
With N,N-dimethyl acetamide; silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride In dichloromethane 1.) -40 deg C, 2.) -40 -> 0 deg C, 1 h, 3.) 0 deg C, 20 h; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With N,N-dimethyl acetamide; silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride In dichloromethane 1.) -40 deg C, 2.) -40 -> 0 deg C, 1 h, 3.) 0 deg C, 24 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With 4 A molecular sieve; 2-methoxyacetic acid; ytterbium(III) triflate In dichloromethane for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With 4 A molecular sieve; 2-methoxyacetic acid; ytterbium(III) triflate In dichloromethane for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With pyridine; dmap In dichloromethane at 25℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With 4 A molecular sieve; 2-methoxyacetic acid; ytterbium(III) triflate In dichloromethane for 4h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trimethylsilyl bromide; 4 A molecular sieve; tetrabutylammomium bromide; cobalt(II) bromide In dichloromethane for 16h; Ambient temperature; Yield given. Yields of byproduct given; | ||
With methanesulfonic acid; tetraethylammonium perchlorate; cobalt(II) bromide In dichloromethane at 25℃; for 2h; Yield given. Yields of byproduct given; | ||
With trimethylsilyl bromide; 4 A molecular sieve; tetrabutylammomium bromide; cobalt(II) bromide In dichloromethane at 22 - 28℃; for 24h; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 13% 2: 60% | With silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride In dichloromethane 1.) -40-0 deg C, 40 min, 2.) 0 deg C, 3 h; | |
With trimethylsilyl bromide; 4 A molecular sieve; tetrabutylammomium bromide; cobalt(II) bromide In dichloromethane for 16h; Ambient temperature; Yield given. Yields of byproduct given; | ||
With methanesulfonic acid; tetraethylammonium perchlorate; cobalt(II) bromide In dichloromethane at 25℃; for 2h; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With trimethylsilyl bromide; 4 A molecular sieve; tetrabutylammomium bromide; cobalt(II) bromide In dichloromethane at 22 - 28℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N,N-dimethyl acetamide; silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride In dichloromethane at -40℃; 2.5 equiv. of N,N-dimethylacetamide; Yield given. Yields of byproduct given; | ||
With N,N-dimethyl acetamide; silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride In dichloromethane 1.) -40 deg C, 2.) -40 -> 0 deg C, 1 h, 3.) 0 deg C, 21 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | ||
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 6h; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With cesium fluoride In acetonitrile for 6h; Ambient temperature; α/β ratio= 2/3; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With trimethylsilyl bromide; 4 A molecular sieve; tetrabutylammomium bromide; cobalt(II) bromide In dichloromethane at 22 - 28℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With N,N-dimethyl acetamide; silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride In dichloromethane at -40℃; 2.5 equiv. of N,N-dimethylacetamide; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With N,N-dimethyl acetamide; silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride In dichloromethane 1.) -40 deg C, 2. -40 -> 0 deg C, 1 h, 3.) 0 deg C, 18 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 16% 2: 21% | With silver trifluoromethanesulfonate; 4-Nitrobenzenesulfonyl chloride In dichloromethane at -40 - 0℃; overnight;; | |
1: 21% 2: 16% | With silver trifluoromethanesulfonate; 4-Nitrobenzenesulfonyl chloride In dichloromethane at -40 - 0℃; overnight at 0 deg C;; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With pivaloyl chloride; triethylamine In acetonitrile at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With acetic anhydride In dimethyl sulfoxide at 20℃; | 2 Preparation of benzyl protected gluconolactone B Dissolve 50g of compound D-4 in 285mL of DMSO and then into it190 mL of acetic anhydride was added and allowed to react at room temperature overnight. The reaction solution was poured into cold water, extracted with ethyl acetate, and washed with saturated sodium hydrogen carbonate solution.Wash with polyester, saturated sodium chloride solution,Dry over anhydrous sodium sulfate.Evaporation on a silica gel column under reduced pressure to give a colorless oilB44g, yield 89%. |
82% | Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranose With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve; Stage #2: With tetrapropylammonium perruthenate In dichloromethane at 20℃; for 2h; | |
82% | Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranose With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve; Stage #2: In dichloromethane at 20℃; for 2h; | XXI 2,3,4,6-Tetra-O-benzyl-D-glucopyranone EXAMPLE XXI 2,3,4,6-Tetra-O-benzyl-D-glucopyranone 4 g freshly activated molecular sieve 4 Å and 3.3 g N-methylmorpholine-N-oxide are added to a solution of 10.0 g 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in 140 ml dichloromethane. The solution is stirred for 20 min at ambient temperature, before adding 0.3 g of tetrapropylammonium perruthenate. After 2 h stirring at ambient temperature the solution is diluted with dichloromethane and filtered through Celite. The filtrate is washed with aqueous sodium thiosulfate solution and water and then dried over sodium sulfate. After the solvent is removed the residue is chromatographed through silica gel (cyclohexane/ethyl acetate 4:1). Yield: 8.2 g (82% of theory) Mass spectrum (ESI+): m/z=539 [M+H]+ |
82% | Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranose With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve; Stage #2: With tetrapropylammonium perruthennate In dichloromethane at 20℃; for 2h; Molecular sieve; | V 2,3,4,6-Tetra-O-benzyl-D-glucopyranone EXAMPLE V 2,3,4,6-Tetra-O-benzyl-D-glucopyranone To a solution of 10.0 g 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in 140 mL dichloromethane are added 4 g freshly activated molecular sieves 4 Å and 3.3 g N-methylmorpholine-N-oxide. The solution is stirred for 20 min at ambient temperature, before 0.3 g tetra-n-propylammonium perruthenate are added. After 2 h stirring at ambient temperature the solution is diluted with dichloromethane and filtered through Celite. The filtrate is washed with aqueous sodium thiosulfate solution and water and then dried over sodium sulfate. After the solvent is evaporated, the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1). Yield: 8.2 g (82% of theory) Mass spectrum (ESI+): m/z=539 [M+H]+ |
82% | Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranose With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve 4A; Stage #2: With tetrapropylammonium perruthennate at 20℃; for 2h; | V To a solution of 10.0 g 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in 140 mL dichloromethane are added 4 g freshly activated molecular sieves 4 Å and 3.3 g N-methylmorpholine-N-oxide. The solution is stirred for 20 min at ambient temperature, before 0.3 g tetra-n-propylammonium perruthenate are added. After 2 h stirring at ambient temperature the solution is diluted with dichloromethane and filtered through Celite. The filtrate is washed with aqueous sodium thiosulfate solution and water and then dried over sodium sulfate. After the solvent is evaporated, the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1). Yield: 8.2 g (82% of theory) Mass spectrum (ESI+): m/z=539 [M+H]+ |
82% | Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranose With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve; Stage #2: With tetrapropylammonium perruthennate In dichloromethane at 20℃; for 2h; | XXIV 4 g freshly activated molecular sieve 4 Å and 3.3 g N-methylmorpholine-N-oxide are added to a solution of 10.0 g 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in 140 ml dichloromethane. The solution is stirred for 20 min at ambient temperature, before adding 0.3 g of tetrapropylammonium perruthenate. After 2 h stirring at ambient temperature the solution is diluted with dichloromethane and filtered through Celite. The filtrate is washed with aqueous sodium thiosulphate solution and water and then dried over sodium sulphate. After the solvent has been eliminated the residue is chromatographed through silica gel (cyclohexane/ethyl acetate 4:1). Yield: 8.2 g (82% of theory) Mass spectrum (ESI+): m/z=539 [M+H]+ |
10.53 g | With acetic anhydride; dimethyl sulfoxide for 12h; | |
With jones reagent In acetone | ||
With acetic anhydride In dimethyl sulfoxide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With Oxalyl bromide In dichloromethane at 20℃; Inert atmosphere; | Synthesis of glycosyl bromides 1 and 6 General procedure: Oxalyl bromide (180mL, 1.3 mmol) was added dropwise to a solution of the corresponding 2,3,4,6-tetra-O-benzyl-D-glycopyranose (540 mg, 1.0 mmol) in anhydrous CH2Cl2 (10 mL). The reaction was stirred at room temperature for about 3 h until disappearance of the starting material by TLC (EtOAc/heptane, 2:5). The mixture was then diluted with CH2Cl2 and washed with water and brine. The organic layer was dried with Na2SO4 and concentrated. The residue was purified by column chromatography (EtOAc/heptane, 2:5) to afford the pure glycosyl bromides as syrups (80% yield of 1 and 74% yield of 6). |
33% | Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranose With triethylamine In dichloromethane at 0℃; for 0.5h; Stage #2: With Oxalyl bromide at 0 - 20℃; | |
With methanesulfonic acid; cobalt(II) bromide In dichloromethane at 25℃; for 1h; |
With cobalt(II) bromide In dichloromethane for 0.5h; Ambient temperature; | ||
With Oxalyl bromide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With diethyl-trichloromethyl-amine In dichloromethane at 25℃; for 4h; | |
89% | With 1,1,1,3,3,3-hexachloro-propan-2-one; triphenylphosphine In neat (no solvent) at 70℃; for 0.75h; | |
83% | With Vilsmeier reagent for 3.5h; Ambient temperature; |
76% | Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranose With triethylamine In dichloromethane at 0℃; for 0.5h; Stage #2: With oxalyl dichloride In dichloromethane at 0 - 20℃; | |
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 0.5h; Ambient temperature; | ||
With thionyl chloride In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 20℃; for 16h; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 42% 2: 20% | With silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride In dichloromethane at -40 - 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With triethylamine In dichloromethane at 25℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With triethylamine In dichloromethane at 25℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With 2-methoxyacetic acid; ytterbium(III) triflate In 1,2-dichloro-ethane at 53℃; for 36h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With 4 A molecular sieve; 2-methoxyacetic acid; ytterbium(III) triflate In dichloromethane for 3h; Heating; | |
90% | With trimethylsilyl bromide; 4 A molecular sieve; tetrabutylammomium bromide; cobalt(II) bromide In dichloromethane at 22 - 28℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluorormethanesulfonic acid In acetic acid at 80℃; for 5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | ||
With sulfuric acid; water; acetic acid for 2h; Reflux; | ||
33.3333 % ee | With hydrogenchloride; acetic acid Inert atmosphere; Reflux; Overall yield = 37 %; Overall yield = 0.61 g; | 4.3. General procedure B: removal of the anomeric methoxy group General procedure: O-Methyl-2,3,4,6-tetra-O-benzyl-pyranoside was dissolved in80% glacial acetic acid/2 M HCl (10:4; 45 mL per gram of pyrano-side) and the reaction mixture was heated under reux for 11 h.Upon completion, the resulting mixture was allowed to reach roomtemperature. Dichloromethane (25 mL per gram of pyranoside) wasadded and the solution was washed using saturated sodiumhydrogenocarbonate (225 mL per gram of pyranoside). Theaqueous layer was extracted using dichloromethane (25 mL pergram of pyranoside). The organic layers were combined, dried us-ing magnesium sulfate and the solvents were removed under re-duced pressure. The residue was puried using silica gel columnchromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With hydrogenchloride In methanol; acetone for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -40 - 0℃; for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -40 - 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -40 - 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With pyridine In methanol at 60℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran | |
62% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With 1H-imidazole; diphenylphosphinopolystyrene; iodine In dichloromethane at 20℃; for 2.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With pyridine; diphenyl phosphite In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With di-tert-butylmethylpyridine; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate In dichloromethane at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With di-tert-butylmethylpyridine; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate In dichloromethane at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With ammonium cerium(IV) nitrate In dichloromethane; acetonitrile at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium hydroxide; tetrabutylammomium bromide In toluene at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With trifluoroacetic acid at 65℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In dichloromethane at 20℃; for 3.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 64% 2: 17% | Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranose With benzyltriethylammonium bromide; p-toluenesulfonyl chloride; 3-hydroxy-2-methyl-1-propene In sodium hydroxide at 20℃; for 34h; Stage #2: With pyridine; sodium periodate; osmium(VIII) oxide In tetrahydrofuran; water at 20℃; for 3h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tert.-butylhydroperoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 16h; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | In acetonitrile at 0℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | Stage #1: 1,1-dimethoxy decane With 2,4,6-trimethyl-pyridine; triethylsilyl trifluoromethyl sulfonate In dichloromethane at 0℃; for 0.5h; Stage #2: 2,3,4,6-tetra-O-benzyl-D-glucopyranose In dichloromethane at 20℃; for 1h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: oxalyl bromide / CH2Cl2; dimethylformamide / 0.5 h / 20 °C 2.1: 95 percent / K2CO3 / 1-methyl-pyrrolidin-2-one / 4 h 3.1: 75 percent / n-BuSH; MgBr2 / diethyl ether; CH2Cl2 / 7 h / 20 °C 4.1: Hg(OCOCF3)2 / tetrahydrofuran / 96 h / 20 °C 4.2: 50 percent / aq. NaOH; NaBH4 / tetrahydrofuran 5.1: 95 percent / H2 / Pd/C / ethyl acetate; methanol / 0.5 h / 20 °C / 760 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: oxalyl bromide / CH2Cl2; dimethylformamide / 0.5 h / 20 °C 2.1: 95 percent / K2CO3 / 1-methyl-pyrrolidin-2-one / 4 h 3.1: 75 percent / n-BuSH; MgBr2 / diethyl ether; CH2Cl2 / 7 h / 20 °C 4.1: Hg(OCOCF3)2 / tetrahydrofuran / 96 h / 20 °C 4.2: 50 percent / aq. NaOH; NaBH4 / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: oxalyl bromide / CH2Cl2; dimethylformamide / 0.5 h / 20 °C 2: 95 percent / K2CO3 / 1-methyl-pyrrolidin-2-one / 4 h 3: 75 percent / n-BuSH; MgBr2 / diethyl ether; CH2Cl2 / 7 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: oxalyl bromide / CH2Cl2; dimethylformamide / 0.5 h / 20 °C 2: 95 percent / K2CO3 / 1-methyl-pyrrolidin-2-one / 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 80 percent / di-tert-butylmethylpyridine; DMTST; MS 4A / CH2Cl2 / 2 h / 20 °C 2: 100 percent / TAS-F / dimethylformamide / 1 h | ||
Multi-step reaction with 2 steps 1: 68 percent / di-tert-butylmethylpyridine; DMTST; MS 4A / CH2Cl2 / 2 h / 20 °C 2: 100 percent / TAS-F / dimethylformamide / 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 80 percent / di-tert-butylmethylpyridine; DMTST; MS 4A / CH2Cl2 / 2 h / 20 °C 2: 100 percent / TAS-F / dimethylformamide / 1 h 3: 100 percent / H2; Amberlite IR-45(OH-) / Pd/C / methanol; ethyl acetate / 5688.78 Torr | ||
Multi-step reaction with 3 steps 1: 68 percent / di-tert-butylmethylpyridine; DMTST; MS 4A / CH2Cl2 / 2 h / 20 °C 2: 100 percent / TAS-F / dimethylformamide / 1 h 3: 100 percent / H2; Amberlite IR-45(OH-) / Pd/C / methanol; ethyl acetate / 5688.78 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In ethanol | 1 EXAMPLE 1 2,3,4,6-Tetra-O-benzyl 1-O-p-nitrobenzoyl D-glucopyranoside 16 (acc. to Methods in Carbohydrate Chemistry, 1972) Batch: 15.5 g 13 (28.7 mmoles) 6 g p-nitrobenzoyl chloride (32.3 mmoles) 3.75 ml pyridine Yield: 15.6 g 16 (78.8% of theory) as white powder M.p.: 93°-98° C. (from ethanol) Recrystallization from diisopropylether gave 16α as needles. M.p.: 122° C. From the mother liquor 16β crystallized, m.p. 98° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sulfuric acid; acetic acid In water for 2h; Reflux; | 2 Preparation of intermediate D-4 60 g of compound D-3 was dissolved in 1000 mL of glacial acetic acid.Then, 126 mL of 1N sulfuric acid was added thereto, and after refluxing for 2 hours,reduced pressure evaporation to dryness to obtain white solid compoundD-457g was obtained (yield: 97%). |
63% | With hydrogenchloride In water; acetic acid at 85℃; for 7h; Reflux; | 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranose (3) To a stirred solution of 2 (50 g, 0.09 mol) in acetic acid (530 mL) at85 °C was added 2N HCl (205 mL) slowly over a period of 1 h. Themixture was refluxed for 6 h and cooled down to room temperatureovernight. The solid which formed upom cooling was filtered off andwashed with H2O (3 × 100 mL) and MeOH (2 × 100 mL) and air driedto give 3 as a white powder. The filtrate was concentrated and theprocess was repeated again to afford another crop of product: Overallyield 31 g, 63% |
41% | With sulfuric acid In methanol; water; acetic acid | 1.1 1. To a stirred solution of above crude compound in glacial acetic acid (700 mL) at 110° C. is added 3N sulfuric acid (120 mL) dropwise during 15 min. After 3 h the reaction mixture is cooled to room temperature and left over night for crystallization of product. The crystals are filtered,washed consecutively with water (4*500 mL) and methanol (2*250 mL), and air dried to afford 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose (115 g, 41% overall two steps) as a white powder (mp 150°-51° C., lit. 151°-152° C.; See, Perrine, T. D. et al. J. Org. Chem. (1967) 32:664). TLC (EtOAC:Hexane 3:7) Rf 0.2. IR (KBr): 3362, 3030, 2911, 2863, 1454, 1357, 1146, 1088 cm-1. 3 H NMR (300 MHz, CDCl3): δ7.38-7.10 (m, 20H), 5.21 (d, J=3.3 Hz, 1H), 4.98-4.44 (m, 9H), 4.25 (m, 1H) 3.72-3.50 (m, 4H). Anal. Calc. for C34 H3606: C, 75.53; H, 6.71. Found: C, 75.68; H, 6.80. |
1 EXAMPLE 1 2,3,4,6-Tetra-O-benzyl α-D-glucopyranose 13 (acc. to Methods in Carbohydrate Chemistry, 1982) Batch: 115 g 10 (207 mmoles) Yield: 54 g 13 (48.3% of theory) M.p.: 152° C. (recrystallized from methanol) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With sulfuric acid In acetic acid | 28.2 28.2. 28.2. 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranose (11) The crude methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 10 (210 g) is dissolved in glacial acetic acid (500 mL) and the solution is heated to nearly boiling. Hot sulfuric acid solution (3N, 130 mL) is added slowly. Heat is periodically increased and more acetic acid (20 mL) is added to dissolve any precipitate. The final cloudy solution is heated at 100°-110° C. for 2 h. After cooling, crude crystalline product is isolated by filtration and washed several times with methanol to yield product 11 as white crystals (109 g, 53%): mp. 168°-170° C. (Lit. 169°-171° C.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; | XVI To a 0 0C solution of 4-(2,3-Difluoro-4-methoxy-benzyl)-5-methyl-1 H-pyrazol-3-ol (2.14 g, 8.4 mmol), 2,3,4,6-tetra-O-benzyl-α-D-gluco-pyranose (4.54 g, 8.4 mmol), and PPh3 (2.20 g, 8.4 mmol) in dry THF (80 ml.) was added diethyl azodicarboxylate in toluene (40%, 3.85 ml_, 8.4 mmol) at a rate such that the solution maintained 2-6 °C. After 10 min the cooling bath was removed, and the reaction solution was stirred at room temperature over night. Then the solution was concentrated at 40 °C under reduced pressure, and the remainder was treated with Et2O (50 ml_). The ether solution was cooled to -18 °C, and the forming precipitate was separated and washed with cold Et2O. The filtrate was diluted with Et2O and washed with aqueous NaOH solution (2 N), water, and brine. After drying over MgSO4 and evaporation of the solvent, the residue was purified by chromatography on silica gel (cyclohexane/EtOAc 2:1->1 :6). The purified product was recrystallized from JPr2O to give the product as a white solid (<5% α anomer). Yield: 3.1O g (48%) ESI-MS: m/z = 777 [M+H]+ |
48% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; | XVI To a 0 0C solution of 4-(2,3-Difluoro-4-methoxy-benzyl)-5-methyl-1 H-pyrazol-3-ol (2.14 g, 8.4 mmol), 2,3,4,6-tetra-O-benzyl-α-D-gluco-pyranose (4.54 g, 8.4 mmol), and PPh3 (2.20 g, 8.4 mmol) in dry THF (80 ml.) was added diethyl azodicarboxylate in toluene (40%, 3.85 ml_, 8.4 mmol) at a rate such that the solution maintained 2-6 0C. After 10 min the cooling bath was removed, and the reaction solution was stirred at room temperature over night. Then the solution was concentrated at 40 0C under reduced pressure, and the remainder was treated with Et2O (50 ml_). The ether solution was cooled to -18 0C, and the forming precipitate was separated and washed with cold Et2O. The filtrate was diluted with Et2O and washed with aqueous NaOH solution (2 N), water, and brine. After drying over MgSO4 and evaporation of the solvent, the residue was purified by chromatography on silica gel (cyclohexane/EtOAc 2:1 ->1 :6). The purified product was recrystallized from iPr2O to give the product as a white solid (<5% α anomer). Yield: 3.1O g (48%)ESI-MS: m/z = 777 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 58% 2: 26% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -40℃; for 0.5h; Inert atmosphere; | |
1: 58% 2: 26% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -40 - -20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In benzene at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With tributylphosphine; diethylazodicarboxylate In benzene at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In benzene at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With tributylphosphine; diamide In benzene at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; acetic acid at 110℃; for 1h; | Synthesis of 2,3,4,5,6-tetra-O-benzyl-D-glucopyranose 20a (FIG. 8);In a flask containing 1-O-methyl-2,3,4,5,6-tetra-O-benzyl-D-glucopyranose 19a (6.4 g; 11.54 mmol) in an acetic acid solution (93 mL), a 3M solution of sulfuric acid (13 mL) is added and the reaction medium is heated to 110 C. for one hour. The reaction is cooled to room temperature. A white precipitate appears and the latter is filtered and dried in ambient air. The compound 20a is obtained very pure as a white solid with a yield of 59% by weight and is directly engaged in the next step without any purification. Characterization of 20a Rf=0.35; eluent: cyclohexane/vinyl acetate (7:3). NMR clearly shows two (?,?) anomers in carbon NMR. 1H NMR (CDCl3, 300 MHz) 3.58-3.66 (m, 4H, H2, H3, 2?H6); 3.94-4.06 (m, 2H, H4, H5); 4.44-4.96 (m, 8H, 4?CH2Ph); 5.21 (d, 1H, 3JH1-H2 3.5, H1); 7.04-7.32 (m, 20H, HAr). 13C NMR (CDCl3, 75 MHz) Majority anomer: 69.0 (C6); 70.6; 73.6; 73.9; 75.4; 76.1; 78.1; 80.4; 82.1; 91.7 (C1); 128.0; 128.1; 128.1; 128.3; 128.4; 128.4 (2C); 128.5; 128.6; 128.8 (2C); 128.8 (2C); 128.9; 138.2; 138.3; 138.6; 139.1. Minority anomer: 69.3 (C6); 75.0; 75.2; 78.2; 83.5; 85.0; 97.9 (C1); 138.1; 138.4; 138.7; 138.9. Melting point: M.p.=151 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium dichloride In methanol at 20℃; for 6h; Inert atmosphere; optical yield given as %de; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium chloride; zinc In acetonitrile for 0.0833333h; Reflux; optical yield given as %de; | 1.2. General experimental procedure General procedure: To a solution of 2,2,2-trichloroethyl 2,3,4,6-tetra-O-acetyl-β-Dglucopyranoside (96 mg, 0.2 mmol) in CH3CN (2 mL), were added Zn powder (104 mg, 1.6 mmol) and NH4Cl (85 mg, 1.6 mmol). After being heated at reflux for 5 min, the mixture was filtered. The filtrate was concentrated to a residue that was purified by silica gel column chromatography (petroleum ether-EtOAc 3:1) to give 2,3,4,6-tetra-O-acetyl-D-glucopyranose (69 mg, 98%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 1h; | |
70% | With sodium hydride In dichloromethane; mineral oil at 20℃; | |
With potassium carbonate In dichloromethane at 20℃; for 72h; | 4-C Preparation of 4-C Preparation of 4-CA mixture of2,3,4,6-tetra-O-benzyl-D-glucopyranose (2.0g, 3.7 mmol), trichloroacetonitrile (2.13 g, 14.8 mmol) andK2C03 (0.66 g, 4.8 mmol) in DCM (13 mE) was stirred atroom temperature for 3 days. The solid was removed by filtration and the filtrate was concentrated to provide a crude product 4-C (3.0 g, >100%) which was used without purification.MS calculated for (C35H35C13N05): 683.2; MS found (M+Na): 708 |
With triethylamine In dichloromethane Inert atmosphere; | 1 Synthesis of Compound 12: The intermediate 11 (1 eqv) was placed in a flask,After nitrogen protection,Dissolved in dichloromethane,Add trichloroacetonitrile (3 eqv) with stirring.Under ice bath, triethylamine (0.1 eqv)After the reaction is complete,Evaporated to dry the solvent on the column,Eluting with a petroleum ether-ethyl acetate mixed solvent,The intermediate 12 was isolated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine at 20℃; for 5h; | I Step I: (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran- 2-yl acetate Step I: (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran- 2-yl acetate To a solution of (2S,3R,4S,5R,6R)-3,4,5-tribenzyloxy-6- benzyloxymethyl)tetrahydropyran-2-ol (5,920 g, 10.95 mmol) in pyridine (21.90 mL) is added acetic anhydride (2.07 mL, 21.9 mmol) dropwise. The reaction is stirred for 5 h at RT then concentrated in vacuo. The crude mixture is diluted in CH2C12 and the resulting solution is washed with HCl IN and brine. The organic phase is dried over Na2S04, concentrated to give a mixture of α/β of [(2R,3R,4S,5R,6R)-3,4,5-tribenzyloxy-6- (benzyloxymethyl)tetrahydropyran-2-yl] acetate as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | A solution of 1.00 mL (2.20 mmol) DEAD (40% in toluene) was addeddropwise over a period of 5 min to a suspension of 0.16 g (1.00 mmol) 2,3-dicyanohydroquinone[40] and 0.58 g (2.20 mmol) PPh3 in 30 mL of dry THFand the mixture was stirred for 10 min at rt. Next, 1.19 g (2.20 mmol) 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranose dissolved in 10 mL of dry THF was addedto the deeply red solution and the mixture was heated under reflux for 3 h.The solution was cooled to rt and the solvent was evaporated under reducedpressure. The residue was purified by column chromatography using a mixtureof toluene and acetone (25:1). Compound 5 was obtained by recrystallizationfrom ethanol/acetone as colorless needles (0.93 g, 77%); m.p. 138-140C(ethanol/acetone); [alpha]D20 = -58.4 (c 1.0, CHCl3); 1H NMR (400 MHz, CDCl3):delta 7.42-7.40 (m, 4 H, Ar-H), 7.36-7.26 (m, 32 H, Ar-H), 7.22-7.19 (m, 6H, Ar-H), 5.16 (d, 2 H, -CH2Ph), 5.02 (d, 2 H, -CH2Ph), 4.99 (d, J1,2 = 7.3 Hz, 2 H,H-1), 4.91-4.85 (m, 6 H, -CH2Ph), 4.59-4.47 (m, 6 H, -CH2Ph), 3.85 (dd, J2,3= 8.8 Hz, 2 H, H-2), 3.79-3.74 (m, 4 H, H-3, H-6a), 3.70-3.61 (m, 6 H, H-4,H-5, H-6b); 13C NMR (100.6 MHz, CDCl3): delta 154.2, 138.2, 137.9, 137.7, 137.7,128.5, 128.5, 128.4, 128.3, 128.0, 128.0, 127.9, 127.8, 127.7, 121.0, 112.8 (54 C,Ar-C), 105.8 (2 C, -CN), 101.2 (2 C, C-1), 84.3 (2 C, C-3), 81.4 (2 C, C-2), 77.3 (2C, C-4), 75.8 (2 C, -CH2-), 75.5 (2 C, C-5), 75.4 (2 C, -CH2-), 75.2 (2 C, -CH2-),73.5 (2 C, -CH2-), 68.7 (2 C, C-6); IR (Neat) vmax 3089, 3062, 3030, 2867, 2230,1497, 1482, 1453, 1363, 1274, 1209, 1071, 1027, 813, 736 cm-1; Anal. calcd. forC76H72N2O12: C 75.73; H 6.02; N 2.32; Found: C 75.92; H 6.00; N 2.30. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70 % de | With potassium fluoride; 1,3-bis(2,6-diisopropylphenyl)-2-fluoroimidazolium tetrafluoroborate In 1,4-dioxane at 80℃; for 18h; Inert atmosphere; Schlenk technique; Sealed tube; Overall yield = 95 %; Overall yield = 51.5 mg; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With N-Bromosuccinimide; water In water; acetone at 20℃; for 0.5h; | 4.c 0.71 mol of p-tolylthiobenzylgalactose was added to 4 mol of acetone, 2 mol of water was added, and 0.94 mol of N-bromosuccinimide was added under stirring at room temperature for 0.5 hour. After completion of the reaction, Treatment to obtain 0.62mol2,3,4,6-tetra-O-benzyl-D-galactopyranose in a yield of 62%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73.3% | With N-Bromosuccinimide; water In acetone at 20℃; for 0.5h; | 3.c 8.25 mol of benzothiazolylthiobenzyl galactose was added to 40 mol of acetone, 20 mol of water was added thereto, and 9.6 mol of N-bromosuccinimide was added thereto at room temperature. The mixture was stirred for 0.5 hour. After completion of the reaction, And 7.33 mol of 2,3,4,6-tetra-oxy-benzyl-D-galactopyranose was obtained in a yield of 73.3%.The aqueous layer was extracted with 50 mol of ethyl acetate. The organic phase was separated by washing the organic phase with 100 mol of water and the organic phase was separated and concentrated. To the mixture was added 10 mol of 2- Tert-butyl methyl ether, filtered, and dried.After the treatment in step b, 50 mol of water was added to the reaction system and the mixture was stirred for 30 minutes. The aqueous layer was extracted with 50 mol of ethyl acetate, and the organic phase was washed with 50 mol of water and washed three times. The organic phase was concentrated and concentrated After the addition, 2 mol of t-butyl methyl ether and 4 mol of isohexane were added to the solution, followed by filtration and drying.The organic layer was separated by adding 30 mol of 5% sodium carbonate solution. The organic layer was separated and the organic layer was separated. Crystallization was carried out by adding 2 mol of t-butyl methyl ether and 3 mol of isohexane, filtering and drying. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40 % de | With potassium <i>tert</i>-butylate In acetonitrile at 20℃; for 2h; diastereoselective reaction; | General procedure for the synthesis of carbohydrate-based vinyl ethers (4a,b)and O-glycosides (7a,b): General procedure: To a solution of β-fluorovinyl sulfone 2a,b (2 mmol) inanhydrousMeCN (15 mL)was added protected sugar (2mmol) and t-BuOK(0.23 g,2 mmol) at room temperature. The reaction mixture was stirred 2h (until 19F NMRspectra displayed complete consumption of the starting material). Then themixturewas diluted with CH2Cl2 (25 mL), water (25 mL) and extracted with CH2Cl2 (2× 25 mL). The organic phase was separated, dried over Na2SO4 and evaporatedunder reduced pressure to give crude 4a,b (70/30 ratio of the E/Z-isomers) or 7a,b(mixture of α/β-anomers of the E/Z-isomers) with 98% yield. Products 4a and 7awere isolated in the pure state in E-isomeric forms by recrystallization from EtOHor MeOH respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With potassium <i>tert</i>-butylate In acetonitrile at 20℃; for 2h; diastereoselective reaction; | General procedure for the synthesis of carbohydrate-based vinyl ethers (4a,b)and O-glycosides (7a,b): General procedure: To a solution of β-fluorovinyl sulfone 2a,b (2 mmol) inanhydrousMeCN (15 mL)was added protected sugar (2mmol) and t-BuOK(0.23 g,2 mmol) at room temperature. The reaction mixture was stirred 2h (until 19F NMRspectra displayed complete consumption of the starting material). Then themixturewas diluted with CH2Cl2 (25 mL), water (25 mL) and extracted with CH2Cl2 (2× 25 mL). The organic phase was separated, dried over Na2SO4 and evaporatedunder reduced pressure to give crude 4a,b (70/30 ratio of the E/Z-isomers) or 7a,b(mixture of α/β-anomers of the E/Z-isomers) with 98% yield. Products 4a and 7awere isolated in the pure state in E-isomeric forms by recrystallization from EtOHor MeOH respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53.846 % de | With cerium(III) chloride; sodium iodide In acetonitrile at 150℃; for 24h; Inert atmosphere; Overall yield = 73 %; | Tert-Butyl Glycoside Cleavage General procedure: The tert butyl glycosides (1 g) was suspended in acetonitrile (20 mL) and stirred at RT for approximately 15 min under an inert atmosphere. Anhydrous CeCl3 (8 eq.) was added followed by NaI (3 eq.) and the reaction mixture was refluxed at 150 oC for 24h. Subsequent to this, the mixture was filtered through a bed of celite and the filtrate collected. Removal of the acetonitrile was afforded in vacuo and the resulting crude was purified using column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
530 mg | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -78 - 20℃; for 18h; | 4.6 4.1.6 3-(4-(1H-Indol-3-yl)-1H-pyrazol-5-yl)-1-(2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole (9) Step 1. Diisopropyl azodicarboxylate (738 μL, 3.75 mmol) was added dropwise to a cooled solution (-78 °C) of 8 (405 mg, 0.91 mmol), triphenylphosphine (1.0 g, 3.81 mmol) and 2,3,4,6-tetra-O-benzyl-α-d-glucopyranose (2.02 g, 3.74 mmol) in THF (25 mL). The mixture was allowed to reach room temperature and stirred for 18 h. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel (gradient from pure cyclohexane to EtOAc/cyclohexane 1:9) yielding β-glucosylated product diastereoisomers (530 mg, TLC Rf = 0.55 (EtOAc/cyclohexane 2:8)) as a colorless oil. The crude product was used in the next step without further purifications. Step 2. In a sealed reaction tube, a solution of the glucosylated intermediate from step 1 (574 mg) and hydrazine monohydrate (1.34 mL, 27.6 mmol) in a 1:1 v/v EtOH/AcOH mixture (6 mL) was heated at 110 °C (oil bath) for 24 h. After cooling, water was added and the mixture was extracted with EtOAc, the assembled organic phases were washed with water, brine, and dried over MgSO4. After evaporation, brown oil was obtained which was dissolved in a minimum of acetone before precipitation by addition of cyclohexane. After evaporation under reduced pressure, the pyrazolone intermediate (523 mg) was obtained as a beige gum used without further purifications. Step 3. To a solution of the pyrazolone intermediate from step 2 (517 mg) and PhNTf2 (355 mg, 0.99 mmol) in CH2Cl2 (8 mL), at 0 °C under argon, was added NEt3 (0.9 mL, 6.5 mmol) and the mixture was allowed to reach room temperature. After 1 h of stirring, solvent was evaporated under reduced pressure. EtOAc was added and the mixture was washed with water, brine and dried over MgSO4. After evaporation, the residue was chromatographed on silica gel (EtOAc/cyclohexane 5:95) yielding the triflate intermediate (380 mg, TLC Rf = 0.39 EtOAc/cyclohexane 2:8, HRMS (ESI+) calcd for C54H48F3N4O8S (M + H)+ 969.3139, found 969.3139) as a pale yellow oil. Step 4. In a sealed reaction tube, a mixture of pyrazolyl triflate from step 3 (380 mg), Pd(OAc)2 (22 mg, 0.098 mmol), dppf (54 mg, 0.098 mmol) and HCO2NH4 (249 mg, 3.95 mmol) in DMF (14 mL) was heated at 90 °C for 2 h. After cooling, EtOAc was added and the mixture was filtered through a Celite pad. The filtrate was washed with water, dried over MgSO4 and evaporated under reduced pressure. The residue was purified by column chromatography (cyclohexane/EtOAc 7:3) yielding compound 9 (122 mg, 0.148 mol, 15% from 8) as a colorless oil. TLC Rf = 0.3 (EtOAc/cyclohexane 4:6); IR (ATR): 3418, 1455, 1361, 1068 cm-1; 1H NMR (500 MHz, CD3CN) δ 3.47 (1H, d, J = 10.5 Hz), 3.62-3.80 (6H, m), 4.10 (1H, d, J = 10.5 Hz), 4.45 (1H, d, J = 12.0 Hz), 4.50 (1H, d, J = 12.0 Hz), 4.61 (1H, d, J = 10.9 Hz), 4.79-4.85 (3H, m), 5.48 (1H, d, J = 8.6 Hz), 6.62-6.65 (2H, m), 6.88 (1H, ddd, J1 = 8.0 Hz, J2 = 7.1 Hz, J3 = 1.0 Hz), 7.00-7.13 (6H, m), 7.19 (1H, ddd, J1 = 8.3 Hz, J2 = 7.1 Hz, J3 = 1.1 Hz), 7.22-7.34 (15H, m), 7.39 (1H, d, J = 8.2 Hz), 7.41 (1H, d, J = 8.2 Hz), 7.43 (1H, s), 7.57 (1H, d, J = 8.3 Hz), 7.74 (1H, d, J = 8.0 Hz), 7.80 (1H, br s), 9.19 (1H, br s), the pyrazole NH was not observed; 13C NMR (126 MHz, CD3CN) δ 69.8, 73.8, 75.0, 75.6, 76.0 (CH2), 78.2, 78.6, 82.0, 85.6, 85.9 (CH), 111.8, 112.4, 120.31, 120.34, 121.5, 122.3, 122.6, 123.4, 124.2, 125.6, 128.44, 128.46, 128.47, 128.6, 128.69, 128.74, 128.90, 128.92, 128.96, 129.2, 129.3, 134.6a (CHarom), 109.0, 110.2, 113.3b, 128.0, 128.1, 137.17, 137.22, 138.5, 139.38, 139.39, 139.8, 140.9b (Carom), between 128.4 and 129.3 ppm, one benzylic CHarom peak could not be observed; a chemical shift measured from a HSQC 1H-13C experiment, b chemical shift measured from a HMBC 1H-13C experiment; HRMS (ESI+) calcd for C53H49N4O5 (M + H)+ 821.3675, found 821.3701. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33.333 % de | With water; bromine In dichloromethane; acetonitrile at 0℃; for 2h; Inert atmosphere; Overall yield = 84 %; Overall yield = 90.8 mg; | General procedure for synthesis of sugar lactols by bromine-mediatedoxidation of thioglycosides General procedure A General procedure: Thioglycosides (0.2 mmol) were dissolved by 1.0 mL acetonitrile in a 10 mLflask, followed by the addition of 0.1 mL water. The mixture was stirred at 0 C for 30 min. 120 mL of Br2(3.0 eq.) solution in CH2Cl2 (5.0 M) was added dropwise and then the yellow mixture was stirred at this temperature until the TLC showed that the substrate was completely consumed. Then the mixture was diluted by 5 mL saturated NaHCO3 aqueous solution and evaporated under reduced pressure to remove acetonitrile. The residue was extracted by CH2Cl2 (10mL 3, for lactol 11 10% n-butanol was usedtogether). The organic layers were combined and dried over anhydrous Na2SO4. The filtrate was concentrated and purified by flash column chromatographyt o give the desired lactols. |
With N-Bromosuccinimide In water; acetone at 20℃; for 8h; Overall yield = 71 percent; Overall yield = 0.78 g; | 2,3,4,6-Tetra-O-benzyl-α/β-d-glucopyranose (16) N-Bromosuccinimide (NBS, 0.44 g, 2.50 mmol, 1.23 eq.) was added to a solution of phenyl 1,2,3,4,6-tetra-O-benzyl-1-thio-β-d-glucopyranoside (15, 1.28 g, 2.03 mmol, 1.00 eq.) in a mixture of acetone/water (30 mL, v/v = 9/1) and stirred at rt for 8 h. The reaction mixture was diluted with water (20 mL) and extracted with diethyl ether (3 × 25 mL). The collected organic phases were washed with sat. NaHCO3 (25 mL), dried over Na2SO4 and the solvent evaporated under reduced pressure. The crude product was purified via column chromatography (pentane/ethyl acetate 4/1 to 2/1) to obtain the desired product as white solid containing both the α- and β-anomer (0.78 g, 1.45 mmol, 71 %). 1H-NMR (360 MHz, CDCl3, 292 K): α+β-Anomer δ (ppm) = 7.37 - 7.24 (m, 18 H), 7.13 (m, 2 H), 5.23 (t, J = 3.0 Hz, 1 H), 4.96 - 4.91 (m, 2 H), 4.85 - 4.78 (m, 2 H), 4.61 - 4.55 (m, 2 H), 4.50 (d, J = 10.8 Hz, 2 H), 4.03 (ddd, J = 10.0, 3.8, 2.0 Hz, 1 H), 3.96 (t, J = 9.3 Hz, 1 H), 3.73 - 3.69 (m, 1 H), 3.66 - 3.57 (m, 3 H). 13C-NMR (101 MHz, CDCl3, 292 K): α+β-Anomer δ (ppm) = 138.8 - 137.9 (CBenzyl), 128.7 - 127.7 (CBenzyl), 97.6, 91.4, 84.7, 83.2, 81.8, 80.1, 77.9, 77.8, 75.8, 75.8, 75.1, 75.13, 74.9, 74.8, 73.6, 73.6, 73.4, 70.4, 69.0, 68.7. Rf 0.15 (pentane/ethyl acetate 4/1) [CAM]. ESI-MS calcd.: 558.2 (+ NH4+), 563.2 (+ Na+) found: 559.2 (+ NH4+), 564.0 (+ Na+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33.333 % de | With water; bromine In dichloromethane; acetonitrile at 0℃; for 2h; Inert atmosphere; Overall yield = 86 %; | General procedure for synthesis of sugar lactols by bromine-mediatedoxidation of thioglycosides General procedure A General procedure: Thioglycosides (0.2 mmol) were dissolved by 1.0 mL acetonitrile in a 10 mLflask, followed by the addition of 0.1 mL water. The mixture was stirred at 0 C for 30 min. 120 mL of Br2(3.0 eq.) solution in CH2Cl2 (5.0 M) was added dropwise and then the yellow mixture was stirred at this temperature until the TLC showed that the substrate was completely consumed. Then the mixture was diluted by 5 mL saturated NaHCO3 aqueous solution and evaporated under reduced pressure to remove acetonitrile. The residue was extracted by CH2Cl2 (10mL 3, for lactol 11 10% n-butanol was usedtogether). The organic layers were combined and dried over anhydrous Na2SO4. The filtrate was concentrated and purified by flash column chromatographyt o give the desired lactols. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium carbonate In acetone for 3h; Inert atmosphere; |
Tags: 6564-72-3 synthesis path| 6564-72-3 SDS| 6564-72-3 COA| 6564-72-3 purity| 6564-72-3 application| 6564-72-3 NMR| 6564-72-3 COA| 6564-72-3 structure
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :