Structure of Allylα-D-galactopyranoside
CAS No.: 48149-72-0
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 48149-72-0 |
Formula : | C9H16O6 |
M.W : | 220.22 |
SMILES Code : | O[C@H]1[C@@H](OCC=C)O[C@H](CO)[C@H](O)[C@@H]1O |
MDL No. : | MFCD01320363 |
InChI Key : | XJNKZTHFPGIJNS-NXRLNHOXSA-N |
Pubchem ID : | 2735272 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.78 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 4.0 |
Molar Refractivity | 49.61 |
TPSA ? Topological Polar Surface Area: Calculated from |
99.38 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.64 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-1.55 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-2.01 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-1.89 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-1.19 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-1.0 |
Log S (ESOL):? ESOL: Topological method implemented from |
0.04 |
Solubility | 239.0 mg/ml ; 1.08 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.03 |
Solubility | 206.0 mg/ml ; 0.934 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
1.44 |
Solubility | 6070.0 mg/ml ; 27.5 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
Yes |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-8.74 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
4.46 |
* 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 |
---|---|---|
88% | With toluene-4-sulfonic acid; at 100℃; for 24h; | 10241] To a stirred suspension of D-galactose 12 (22.2 g, 123 mmol) in allyl alcohol (250 mE) was added para-toluenesulfonic acid (2.3 g, 12.09 mmol). The mixture was heated to 1000 C. and stirred for 24 h after which it was cooled to r.t. and quenched by the addition of NEt3. The solvent was removed in vacuo and the crude product was co-evaporated twice with toluene and purified by flash column chromatography on silica gel (gradient CH2Cl2/MeOH9: 1 -4: 1). Recrystalization from EtOAc yielded galactoside 13 (22.2 g, 88%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With camphor-10-sulfonic acid; at 20℃; for 48h;Inert atmosphere; | Allyl- a - D -galactopyranoside 11 (5.00 g, 22.73 mmol,1 equiv) anddry camphorsulfonic acid (0.26 g, 1.14, 5 mol %) were dissolved in2,2-dimethoxypropane under nitrogen atmosphere. The mixturewas stirred for 48 h at room temperature. Triethylamine was thenadded and the mixture was stirred for a further 15 min. The sol-vents were removed under reduced pressure. The residue was thendissolved in methanol/water (10:1) and the resulting solution washeated under reux for 7 h. The solvents were then removed underreduced pressure and the residue was puried using silica gelcolumn chromatography (light petroleum/ethyl acetate 2:3) to givethe desired product (3.93 g, 67%) as a colourless solid.Mp 139 e 140C (lit. Mp 138 e 142C); [ a ]D22148.7 (c 1.0, CHCl3),lit. [ a ]D25131.5 (c 1.0, CHCl3); nmax (neat)/cm13403, 2931, 2359,2340, 1643, 1074, 1039, 871, 688; dH (400 MHz, CDCl3) 2 e OH ex-change, 1.35 (3H, s, CH3),1.51 (3H, s, CH3), 3.75 e 3.85 (2H, m, H-2, H-6A), 3.90 (1H, dd, J6b,5 6.4 Hz, J6b,6a 11.8 Hz, H-6b), 4.07 e 4.10 (2H,m, H-5, e OCHHCHX ] CH2), 4.23 e 4.29 (3H, m, 2CH, e OCHHCHX ]CH2), 4.94 (1H, d, J1,2 3.6 Hz, H-1), 5.23 (1H, dd, JA,B 1.6 Hz,JA,X 10.4 Hz, e OCH2CHX ] CHAHB), 5.29 (1H, dd, JB,A 1.6 Hz,JB,X 15.6 Hz, e OCH2CHX ] CHAHB), 5.85 e 6.00 (1H, m, e OCH2CHX ]CH2); dC (100 MHz, CDCl3) 25.6 (CH3), 27.8 (CH3), 62.6 (CH2), 68.2(C-3), 68.3 (CH2), 69.6 (C-2), 73.9 (CH), 76.3 (CH), 96.8 (CH), 109.8(C), 117.9 (CH2), 135.6 ( e OCH2CHX ] CH2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Ozone was bubbled through a solution of allyl glycoside 16 (250 mg)in MeOH (75 mL) at -78 C until the solution turned blue (ca. 25 min). The solution was purged under N2 flow to remove the excess of ozone, and dimethyl sulfide (1 mL) was added. After a few minutes, nitrogen was again passed through the solution, which was then allowed to warm to r.t. The solvent was removed under reduced pressure to afford glycosyl aldehydes 29-39 (quant.) as a colorless oil. O-Benzylhydroxylamine hydrochloride (1.1 equiv) was then added to the solution of the corresponding glycosyl aldehydes (10 mg, 1 equiv) in H2O (1 mL). The mixture was stirred at 40 C for 30 min and the final oxime was purified by semipreparative HPLC to obtain the Z/E mixture of neoglycoconjugates 47-58. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
STEP 1 : (4aR,6S,7R,8R,8aR)-6-(allyloxy)-2-phenylhexahydropyrano[3,2- d][1,3]dioxine-7,8-diol Into a 3-L 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed (2R,3R,4S,5R,6S)-2-(hydroxymethyl)- 6-(prop-2-en-1 -yloxy)oxane-3,4,5-triol (80 g, 363.27 mmol, 1.00 equiv), CSA (250 mg), (dimethoxymethyl)benzene (82 g, 538.80 mmol, 1.48 equiv), CHCI3 (1.2 L). The resultant suspension was placed in a preheated oil bath (bath temp. 90 C), and the distillate was collected. After approximately 15 ml was collected, the same volume of CHCb was added. This process was repeated. The reaction progress was monitored by TLC. The resulting mixture was washed with 1x500 ml of water and 1x500 ml of saturated aqueous sodium bicarbonate. The resulting mixture was washed with 1x500 ml of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The resulting residue was washed with PE/EA(20: 1) to yield (4aR,6S,7R,8R,8aR)-2-phenyl-6-(prop-2-en-1 -yloxy)-hexahydro-2H-pyrano[3,2- d][1,3]dioxine-7,8-diol as a white solid. 1 H NMR: (300 MHz, CDCI3): delta 7.54- 7.47(m, 2H), 7.41 -7.34(m, 3H), 5.99-5.86(m, 1H), 5.55(s, 1H), 5.34-5.21 (m, 2H), 5.09(s, 1H), 4.29-4.21 (m, 3H), 4.1 1 -4.05(m, 2H), 3.93(s, 2H), 3.74(s, 1H). LC-MS (ES, m/z): 634.2 [2M+NH4] + | ||
With camphorsulfonic acid; In acetonitrile; for 20h; | Small-scale synthesis: To a solution of allyl alpha-D-galactopyranoside (1.0 g, 4.51 mmol) in acetonitrile (25 ml) was added p-methoxybenzaldehyde dimethyl acetal (1.65 g, 9.08 mmol) followed by CSA (105 mg, 0.45 mmol). After 20 h, Et3N (0.1 ml) was added and the solvent was removed under reduced pressure and the residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc three times and the combined organic extracts were washed with brine, dried with Na2S04, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (40 g column, EtOAc/heptane: 0>20%>100%, Teledyne ISCO Combiflash) to yield a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With pyridine; at 20℃; for 18h;Inert atmosphere; | Example 27 Synthesis of allyl 6-O-trityl-alpha-D-galactopyranoside (27*) 1-O-Allyl-galactoside (Org. Lett. 2002, 4, 489) (4 g, 18.2 mmol) was dissolved in pyridine (18 mL). To the solution was added trityl chloride (6.58 g, 23.6 mmol) and the mixture was stirred at r.t. for 18 h after which the solvent was removed in vacuo. The crude product was purified by flash column chromatography on silica gel (CH2Cl2/MeOH = 10:1) to yield pyranoside 27* (7.0 g, 83%) as colorless oil. [alpha]Dr.t. = +60.0 (c = 1, CHCl3); Rf = 0.8 (CH2Cl2/MeOH = 5:1); IR (film) vmax 3402, 2929, 1491, 1449, 1218, 1152, 1070, 1032, 746, 703 cm-1; 1H NMR (400 MHz, CDCl3) delta 7.51-7.18 (m, 15H), 5.99-5.88 (m, 1H), 5.25 (ddq, J = 35.9, 10.4, 1.4 Hz, 2H), 4.95 (d, J = 3.8 Hz, 1 H), 4.25 (ddt, J = 12.8, 5.4, 1.4 Hz, 1H), 4.05 (ddt, J = 12.8, 6.3, 1.3 Hz, 1 H), 3.96 (s, 1 H), 3.89 (t, J = 5.8 Hz, 1 H), 3.81 (d, J = 5.7 Hz, 1 H), 3.75 (d, J = 9.8 Hz, 1H), 3.47 (s, 1 H), 3.43 (dd, J = 9.8, 6.1 Hz, 1 H), 3.32 (dd, J = 9.8, 5.3 Hz, 1 H), 2.86 (d, J = 2.1 Hz, 1 H), 2.71 (d, J = 8.1 Hz, 1 H); 13C NMR (75 MHz, CDCl3) delta 143.8, 133.7, 128.6, 127.8, 127.1, 117.8, 97.5, 86.9, 71.2, 69.8, 69.5, 69.5, 68.5, 63.3; HR ESI Calcd for C25H25O5 [M+Na+]: 485.1935 found: 485.1941. |
83% | With pyridine; at 20℃; for 18h;Inert atmosphere; | Example B.15: Synthesis of allyl 6-O-thtyl-alpha-D-galactopyranoside (27*)1 -O-Allyl-galactoside {Org. Lett. 2002, 4, 489) (4 g, 18.2 mmol) was dissolved in pyridine (18 mL). To the solution was added trityl chloride (6.58 g, 23.6 mmol) and the mixture was stirred at r.t. for 18 h after which the solvent was removed in vacuo. The crude product was purified by flash column chromatography on silica gel (CH2CI2/MeOH = 10:1 ) to yield pyranoside 27* (7.0 g, 83%) as colorless oil. [a]Dr t = +60.0 (c = 1 , CHCI3); Rf = 0.8 (CH2CI2/MeOH = 5:1 ); IR (film) vmax 3402, 2929, 1491 , 1449, 1218, 1 152, 1070, 1032, 746, 703 cm"1; 1H NMR (400 MHz, CDCI3) delta 7.51-7.18 (m, 15H), 5.99-5.88 (m, 1 H), 5.25 (ddq, J = 35.9, 10.4, 1 .4 Hz, 2H), 4.95 (d, J = 3.8 Hz, 1 H), 4.25 (ddt, J = 12.8, 5.4, 1 .4 Hz, 1 H), 4.05 (ddt, J = 12.8, 6.3, 1 .3 Hz, 1 H), 3.96 (s, 1 H), 3.89 (t, J = 5.8 Hz, 1 H), 3.81 (d, J = 5.7 Hz, 1 H), 3.75 (d, J = 9.8 Hz, 1 H), 3.47 (s, 1 H), 3.43 (dd, J = 9.8, 6.1 Hz, 1 H), 3.32 (dd, J = 9.8, 5.3 Hz, 1 H), 2.86 (d, J = 2.1 Hz, 1 H), 2.71 (d, J = 8.1 Hz, 1 H); 13C NMR (75 MHz, CDCI3) delta 143.8, 133.7, 128.6, 127.8, 127.1 , 1 17.8, 97.5, 86.9, 71 .2, 69.8, 69.5, 69.5, 68.5, 63.3; HR ESI Calcd for C25H2505 [M+Na+]: 485.1935 found: 485.1941 . |
83% | With pyridine; at 20℃; for 18h; | 10242] 1-0-Allyl-galactoside 13 (4 g, 18.2 mmol) was dissolved in pyridine (18 mE). To the solution was added trityl chloride (6.58 g, 23.6 mmol) and the mixture was stirred at r.t. for 18 h after which the solvent was removed in vacuo. The crude product was purified by flash column chromatography on silica gel (CH2Cl2/MeOH10: 1) to yield pyranoside 14 (7.0 g, 83%) as colorless oil. [a]Dt+60.0 (c1, CHC13); R1O.8 (CH2Cl2/MeOH5:1); IR (film) vm,x 3402, 2929, 1491,1449,1218,1152,1070, 1032,746,703cm?; ?HNMR (400 MHz, CDC13) oe 7.51-7.18 (m, 15H), 5.99-5.88 (m, 1H), 5.25 (ddq, J35.9, 10.4, 1.4 Hz, 2H), 4.95 (d, J3.8 Hz, 1H), 4.25 (ddt, J12.8, 5.4, 1.4 Hz, 1H), 4.05 (ddt, J12.8, 6.3, 1.3Hz, 1H), 3.96 (s, 1H), 3.89 (t, J5.8 Hz, 1H), 3.81 (d, J5.7Hz, 1H), 3.75 (d, J9.8 Hz, 1H), 3.47 (s, 1H), 3.43 (dd, J9.8,6.1 Hz, 1H), 3.32 (dd, J9.8, 5.3 Hz, 1H), 2.86 (d, J2.1 Hz,1H), 2.71 (d, J8.1 Hz, 1H); ?3C NMR (75 MHz, CDC13) oe143.8, 133.7, 128.6, 127.8, 127.1, 117.8, 97.5, 86.9, 71.2,69.8, 69.5, 69.5, 68.5, 63.3; HR ESI Calcd for C25H2505[M+Na]: 485.1935. found: 485.1941. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | For allyl 3-O-methyl-alpha-D-galactopyranoside (15), a micro-wave vial was filled with allyl galactoside 14 (57 mg, 0.26 mmol) and dibutyltinoxide (71 mg, 0.29 mmol), and the reagents were dried in vacuo. Dry PhMe/MeCN (5:1, 660l) was added,and the suspension in the sealed tube was exposed to microwave irradiation for 20 min at 150 C. The clear solution was allowed to cool to 50 C, and to the resulting suspension was added MeI (405l,6.5mmol)dropwise.The reaction was stirred for 48h at 50 C, after removal of the volatiles in vacuo and purification ofthe crude product by MPLC, the title compound was obtained as a pure product (40 mg, 65%). 1H NMR (400 MHz, MeOH-d4 )6.08-5.89(m,1H,CH 2CHCH 2 O-), 5.34 (dd, J 17.2, 1.8 Hz,1H, CH2 CHCH 2 O-), 5.17 (dd, J 10.4, 1.6 Hz, 1H,CH2 CHCH 2 O-), 4.85 (d, J 4.0 Hz, 1H, H1), 4.23 (ddt, J 13.0,5.3, 1.6 Hz, 1H, 1H, CH 2 CHCH2 O-), 4.13 (dd, J 3.3, 1.2 Hz,1H, H4), 4.04 (ddt, J 13.0, 6.1, 1.4 Hz, 1H, CH 2 CHCH2 O-),3.85 (dd, J 10.1, 3.9 Hz, 1H, H2), 3.82-3.77 (m, 1H, H5),3.76-3.63 (m, 2H, H6), 3.46 (s, 3H, CH 3 ), 3.42 (dd, J 10.1, 3.2Hz, 1H, H3). 13C NMR (101 MHz, MeOH-d4)135.65(CH 2CHCH 2 O-), 117.50 (CH 2 CHCH 2 O-), 99.37 (C1), 81.15(C3), 72.35 (C5), 69.38 (CH 2 CHCH 2 O-), 69.22 (C2), 66.91 (C4),62.74 (C6), 57.24 (CH 3 ). Transcripts of NMR spectra are shownin supplemental Figs. 6 and 7). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Route a: 1-O-(2-propenyl)-alpha-D-galactose (II) Into 140 mL of allyl alcohol, 50.0 grams (278 mmol) of D-galactose (I) was added and sufficiently dissolved therein. To the solution, 0.5 mL of trifluoromethanesulfonic acid was gradually added under an ice-cooled condition. Then, the solution was reacted in an oil bath at 80 C. for 24 hours while stirring. At the stage where the reaction sufficiently proceeded, the reaction mixture was neutralized with 1.0 mL of triethylamine, concentrated in vacuo, and purified by silica gel flash chromatography (chloroform: methanol=6:1?5:1?4:1), to give a pale yellowish oily substance. The product was dissolved in hot ethanol and cooled to crystallize it, to give a colorless and needle crystal (yield 16.6 g, 75.5 mmol, recovery: 27.2%). m.p.;145-148 C. [alpha]D=+172.2 (c 0.97, CHCl3) |