Home Cart Sign in  
Chemical Structure| 1461750-25-3 Chemical Structure| 1461750-25-3
Chemical Structure| 1461750-25-3

(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-tetrahydro-6-methylpyran-2-one

CAS No.: 1461750-25-3

4.5 *For Research Use Only !

Cat. No.: A484888 Purity: 97%

Change View

Size Price

US Stock

Global Stock

In Stock
50mg ł§§¶ÊÊ Inquiry Inquiry
100mg łÿ˶ÊÊ Inquiry Inquiry
250mg łóď¶ÊÊ Inquiry Inquiry
1g łËÇď¶ÊÊ Inquiry Inquiry

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 50mg

    ł§§¶ÊÊ

  • 100mg

    łÿ˶ÊÊ

  • 250mg

    łóď¶ÊÊ

  • 1g

    łËÇď¶ÊÊ

In Stock

- +

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support Online Technical Q&A
Product Citations

Alternative Products

Product Details of [ 1461750-25-3 ]

CAS No. :1461750-25-3
Formula : C27H28O5
M.W : 432.51
SMILES Code : O=C1[C@H](OCC2=CC=CC=C2)[C@@H](OCC3=CC=CC=C3)[C@H](OCC4=CC=CC=C4)[C@@H](C)O1
MDL No. :MFCD29924782
InChI Key :SFKYGYRKFMUHAD-YEHREXKJSA-N
Pubchem ID :76286534

Safety of [ 1461750-25-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 1461750-25-3 ]

* 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.

  • Downstream synthetic route of [ 1461750-25-3 ]

[ 1461750-25-3 ] Synthesis Path-Downstream   1~29

  • 3
  • 2,3,4-tri-O-benzyl-6-deoxy-D-glucopyranose [ No CAS ]
  • [ 1461750-25-3 ]
YieldReaction ConditionsOperation in experiment
98% With acetic anhydride; In dimethyl sulfoxide; at 20℃; To a solution of compound 48 (25.20g, 57.99mmol) in DMSO (200mL) was added acetic acid anhydride (50mL). The mixture was stirred overnight before diluted with water, then sat. aq. NaHCO3 was added into the mixture until no gas generated. The mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, concentrated in vacuo, and purified by column chromatography on silica gel (petroleum ether/EtOAc=10/1) to give compound 49 (24.70g, 98%) as a white solid. 1H NMR (400MHz, Chloroform-d) δ 7.48-7.19 (m, 15H), 4.95 (d, J=11.5Hz, 1H), 4.74-4.61 (m, 3H), 4.61-4.48 (m, 3H), 4.12 (d, J=5.0Hz, 1H), 3.97-3.87 (m, 1H), 3.46 (dd, J=8.8, 5.7Hz, 1H), 1.41 (d, J=6.4Hz, 3H). LRMS (ESI, m/z): 433 [M+H]+.
91% With Iodine monochloride; caesium carbonate; In dichloromethane; at 0 - 20℃; for 5h;Green chemistry; General procedure: Starting alcohols (1.00 g, 1.0 eq) specified in Table 3 were dissolved in 10 mL of dried CH2Cl2 (for substrates in entries 8-20 in Table 3, 30 mL of dried CH2Cl2 was used), and the resulting mixture was stirred in an ice-water bath, followed by addition of Cs2CO3 (3.0 eq). The suspension was stirred at this temperature, and ICl (1.5 eq) dissolved in 2 mL of CH2Cl2 was added dropwise. After addition, the reaction mixture was stirred at room temperature until the reaction completed as indicated by TLC analysis, which was conducted at 0.5-h intervals.The reaction mixture was subjected to aqueous workup described previously to yield the pure carbonyl compounds specified in Table 3.
80% In dimethyl sulfoxide; at 23 - 25℃; S5: The crude product of compound F is obtained by passing compound E through swern oxidation reaction:Add 400mL DMSO into the reaction flask, and add 200mL acid anhydride dropwise at 23, and then dissolve 79g of compound E obtained in step S4 in 160mL DMSO and then drop it into the reaction flask, react at 25, and pass thin layer chromatography. (Developing solvent is EA/PE=5/1; 2mL) It is detected that compound E has basically disappeared, the reaction solution is poured into 2L ice water to quench the reaction, stirred for 0.5h, extracted with 200mL ethyl acetate 3 times, and the ethyl acetate phase is used 100 mL of 10% sodium chloride aqueous solution was washed twice, 300 mL of saturated sodium bicarbonate solution was washed once, 200 mL of saturated brine was washed once, concentrated and dried to obtain a crude product of compound F;S6: Add the crude product of compound F obtained in step S5 to 200 mL of ethanol, heat to reflux to dissolve, cool down to crystallize, and filter with suction to obtain 62 g of purified compound F.
With acetic anhydride; In dimethyl sulfoxide; at 20℃; 80 mL of dimethyl sulfoxide(DMSO) is added into a 250 mL of round-bottom flask, and cooled with ice water bath. 50 mL of acetic anhydride(Ac2O) is added dropwise slowly under stirring,, and stirred for another half an hour at this temperature after addition. After that, the solution prepared by dissolving 13.04 g(30 mmol) of M-3 in 20 mL of DMSO is added dropwise slowly, and then stirred at room temperature until the TLC shows that the reaction completes. After the reaction completes, the reaction mixture is dumped into 500 mL of ice water, stirred for half an hour, the pH value is adjusted to pH = 4-6 with saturated aqueous NaHCO3 solution, and extracted with 100 mL x 3 of dichloromethane. The organic phases are combined, washed with 0.1 mol/l aqueous NaCl solution, dried with anhydrous sodium sulfate, and evaporated to dryness on the rotary evaporator, the resulting residue is purified by column chromatography to obtain the pure productM-4. M-4 is a white solid, has a melting point of 66-67C, the 1H-NMR (400 MHz, CDCl3) of which are as follows: δ 7.22-7.38 (m, 15H), 4.92 (d, 1H, J = 11.2 Hz), 4.68 (d, 1H, J = 11.2 Hz), 4.64 (d, 1H, J = 11.6 Hz), 4.62 (d, 1H, J = 11.6 Hz), 4.50-4.56 (m, 3H), 4.10 (d, 1H, J = 4.8 Hz), 3.88 (t, 1H, J = 5.4 Hz), 3.44 (dd, 1H, J = 5.6 Hz and 8.8 Hz), 1.39 (d, 3H, J = 6.4 Hz). Moreover, 13C-NMR (100 MHz, CDCl3) of M-4 is as follows: δ 168.99, 137.36, 137.30, 136.77, 128.48, 128.45, 128.43, 128.34, 128.14, 127.99, 127.93, 81.36, 81.15, 77.29, 74.58, 73.48, 73.21, 72.97, 18.27.

  • 4
  • [ 1461750-25-3 ]
  • C43H45ClO6 [ No CAS ]
  • 5
  • [ 1461750-25-3 ]
  • [ 1461750-26-4 ]
  • 7
  • [ 1461750-25-3 ]
  • [ 1461750-27-5 ]
  • [ 1461750-28-6 ]
  • 8
  • [ 1461750-25-3 ]
  • [ 1461750-28-6 ]
  • 9
  • [ 461432-23-5 ]
  • [ 1461750-25-3 ]
  • C42H43ClO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% Take 112g of compound N-9 (0.347mol, 1.25eq) and 720ml of anhydrous tetrahydrofuran and stir, replace with nitrogen three times, cool down and control the temperature -80-75, and add 240ml 1.6M n-butyllithium n-hexane solution ( 0.347mol, 1.25eq), the dripping time is 2h, after dripping, keep stirring for 1h; continue to control the temperature -80-75, add dropwise the tetrahydrofuran solution of compound N-8 (120g compound N-8 (0.277mol, 1.0eq) dissolved in 240ml tetrahydrofuran), the dripping time is 2h, after dripping, keep stirring for 2h until TLC monitors that the reaction is complete (petroleum ether: ethyl acetate=6:1 as the developing solvent, and no compound N-8. Complete); Control the temperature to below -20C, add dropwise 600ml, 10wt% ammonium chloride aqueous solution, then return to 10C, extract with 1600ml dichloromethane, take the organic phase, wash with 1500ml saturated brine, and dry with anhydrous sodium sulfate , Concentrate under reduced pressure to no cuts to obtain 250 g of compound N-10-a, which is continuously cast in step S2 at a yield of 100%.
  • 11
  • methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside [ No CAS ]
  • [ 1461750-25-3 ]
  • 12
  • methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside [ No CAS ]
  • [ 1461750-25-3 ]
  • 14
  • [ 1461750-25-3 ]
  • C5H9NO2*C21H25ClO5 [ No CAS ]
  • 15
  • [ 461432-23-5 ]
  • [ 1461750-25-3 ]
  • C43H45ClO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a 250 mL of dry round-bottom flask, 6.51 g (20 mmol) of (2-chloro-5-bromophenyl) (4-ethoxyphenyl) methane and 60 mL of dry THF are added, and the magneton is added. After purging with nitrogen gas, the mouth of the round-bottom flask is sealed with a soft rubber plug. The flask is placed in a liquid nitrogen-ethanol system to cool to -78C, and stirred. 12.5 mL of n-butyl lithium solution with a concentration of 1.6 M (20 mmol n-butyl lithium) is added slowly with a injector, , and stirred for another half an hour at this temperature after the addition, and then the solution prepared by dissolving 8.65 g (20 mmol) of M-4 in 40 mL of dry THF is added slowly with a injector. After the addition, the reaction mixture is stirred for another 1 hour at this temperature. After which, at this temperature, the solution prepared by dissolving 4.81 g (50 mmol) of methanesulfonic acid in 20 mL of methanol is added slowly with a injector, , and stirred at room temperature for 12 hours after the addition. (0266) The reaction mixture is dumped into 400 mL of ice water, stirred, the pH value is adjusted to pH = 4-6 with saturated NaHCO3 solution, and extracted with 100 mL x 3 of dichloromethane. The organic phases are combined, washed with 0.1 mol/l aqueous NaCl solution, and dried with anhydrous sodium sulfate, evaporated to dryness on the rotary evaporator, and the resulting residue is the crude product of M-5. The crude product of M-5 is analyzed using electrospray ionization-mass spectrometry (ESI-MS), the mass-charge ratio of which is m/z = 693 ([M+H]+). Wherein, the crude product can be used for the next step of reaction without purification.
  • 16
  • [ 75-75-2 ]
  • [ 1030825-20-7 ]
  • [ 1461750-25-3 ]
  • C46H45FO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
A 2L dry round bottom flask was added 36.1g (0.1 mol) compound I-1 and 600 ml dry THF. Add magnetic stirrer. After nitrogen purging, soft rubber plug sealing. The flask placed in liquid nitrogen - ethanol system cooled to -78 C. Start the electromagnetic stirring. Using syringe slowly drop 62.5 ml (0.1mmol) 1.6M n-BuLi. After completion of the dropping, at this temperature continue stirring for half an hour. And then through the syringe slowly drop 43.3g (10mmol) II dissolved in 200 ml dry THF prepared solution. After the completion of the dropping, the reaction mixture at this temperature is continuously stirred for 1 hour. Under ice water bath cooling, through the dropping funnel slowly drop 28.8g (0.3 mol) methanesulfonic acid dissolved in 200 ml methanol prepared solution. After dropping, stir at room temperature overnight. The reaction mixture dumping to 4000 ml ice water, stirring, saturated NaHCO3 Solution to adjust pH=4 - 6,500 ml × 3 of methylene chloride extraction. The combined organic phase, dilute salt water washing, drying with anhydrous sodium sulfate, evaporated on the rotary evaporator, the residue is crude III. The crude product purification is not used, directly used for the next step reaction.
  • 17
  • [ 1461750-25-3 ]
  • 4-(6-deoxy-β-D-glucopyranosyl)-2-[5-(4-fluorophenyl)thiophen-2-ylmethyl]-1-methylbenzene [ No CAS ]
  • 18
  • [ 1461750-25-3 ]
  • C45H43FO4S [ No CAS ]
  • 19
  • C27H30O5 [ No CAS ]
  • [ 1461750-25-3 ]
YieldReaction ConditionsOperation in experiment
100% With acetic anhydride; dimethyl sulfoxide; In dimethyl sulfoxide; at 20 - 30℃; for 10h;Large scale; added in 1000L reactorTri-O-benzyl-6-deoxy-D-pyran methyl glucose205 kg (472 mol), dimethylsulfoxide (DMSO) 460 kg (5888 mol),Control the temperature of 20-30 C was dropped 230kg acetic anhydride (2253mol)Reaction 10h, the chromatographic track to the end of the reaction,Add a small amount of water, heating and decompression recovery dimethyl sulfide,Acetic acid,DMSO to no distillate,Cooling to 50 , adding 50% aqueous solution of ethanol 300kg,Fully stirred, cooled and filtered,Tri-O-benzyl-6-deoxy-D-glucopyranoso-1,5-lactone was obtained as a crude product,Then recrystallized 690kg ethanol, filtered,Get it dryTri-O-benzyl-6-deoxy-D-glucopyranoso-1,5-lactone204kg, the yield was 100%Purity is 99.5%.
  • 20
  • C29H34O8S [ No CAS ]
  • [ 1461750-25-3 ]
  • 21
  • [ 639504-92-0 ]
  • [ 1461750-25-3 ]
  • 22
  • [ 1461750-25-3 ]
  • C17H25BrO [ No CAS ]
  • C44H54O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
A 1 L dry round bottom flask was charged with 32.5 g (0.1 mol)Compound I and 300 mL of dry THF,Add a magnet, purged with nitrogen gas soft rubber stopper seal.The flask was placed in liquid nitrogen - ethanol system was cooled to -78 ,Start electromagnetic stirring.A solution of 62.5 mL (0.1 mol)1.6M of n-butyl lithium,After the addition was complete, stirring was continued at this temperature for half an hour,Then, 43.3 g (0.1 mol) of II was slowly dropped through a syringeDissolved in 200 mL of dry THF.The reaction mixture was stirred for a further hour at this temperature,Then slowly warmed to room temperature for 1 hour.The reaction mixture was poured into 400 mL of ice water, stirred and extracted with saturated NaHCO3 solution adjusted to pH = 4-6 and 100 mL × 3 of dichloromethane. Combined organic phase, dilute brineWashed, dried over anhydrous sodium sulphate and evaporated to dryness on a rotary evaporator. The residue is the crude product of III-M.The crude product without purification, used directly for the next reaction.
  • 23
  • [ 1461750-25-3 ]
  • C44H54O5 [ No CAS ]
  • 24
  • [ 1461750-25-3 ]
  • [ 1431771-67-3 ]
  • 26
  • (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ol [ No CAS ]
  • [ 1461750-25-3 ]
YieldReaction ConditionsOperation in experiment
98% With acetic anhydride; In dimethyl sulfoxide; at 20℃; Compound 1-5 (25.20 g, 57.99 mmol) was dissolved in 200 mL of DMSO, 50 mL of acetic anhydride was added at room temperature. After the addition was completed, stirred at room temperature overnight. TLC monitored (UV color) that the reaction was completed, then saturated sodium bicarbonate solution was slowly added until no bubbles were formed. The mixture was extracted with ethylacetate. The combined organic layers were washed twice with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography (petroleum ether / ethylacetate 10/1, v/v) to provide 24.70g white solid 1-6 in 98% yield. 1H NMR (400 MHz, Chloroform-d) δ 7.48 - 7.19 (m, 15H), 4.95 (d, J = 11.5 Hz, 1H), 4.74 - 4.61 (m, 3H), 4.61 - 4.48 (m, 3H), 4.12 (d, J = 5.0 Hz, 1H), 3.97 - 3.87 (m, 1H), 3.46 (dd, J = 8.8, 5.7 Hz, 1H), 1.41 (d, J = 6.4 Hz, 3H). LRMS (ESI, m/z): 433 [M+H]+.
  • 27
  • [ 1461750-25-3 ]
  • (1S,3’R,4’S,5’S,6’R)-6’-methyl-6-(4-methylbenzyl)-3’,4’,5’,6’-tetrahydro-3H-spiro[isobenzofuran-1,2’-pyran]-3’,4’,5’-triol [ No CAS ]
  • 28
  • [ 1461750-25-3 ]
  • (1S,3'R,4'S,5'R,6'R)-3',4',5'-tri(benzyloxy)-6'-methyl-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-6-formaldehyde [ No CAS ]
  • 29
  • [ 1461750-25-3 ]
  • C42H42O6 [ No CAS ]
 

Historical Records

Technical Information

Categories