methyl 2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-α-D-glucopyranoside
• CAS No.: 495378-99-9
• Molecular Formula: C₃₅H₄₈O₇Si
• Molecular Weight: 608.847
• Mol file: 495378-99-9.mol

Synonyms:methyl 2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-α-D-glucopyranoside

Chemical Property of methyl 2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-α-D-glucopyranoside

There total 3 articles about methyl 2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-α-D-glucopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-ol (111727-15-2) + p-methoxybenzyl chloride (824-94-2) → methyl 2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-α-D-glucopyranoside (495378-99-9)

Guidance literature:

With potassium hydroxide; tetrabutylammomium bromide; In toluene;

DOI:10.1016/S0008-6215(02)00139-8

Reference yield: 84.0%

4-methoxybenzyl N-allyl thiocarbamate (1616487-09-2) + (2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-ol (111727-15-2) → 5-bromomethyl-thiazolidin-2-one (89033-67-0) + methyl 2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-α-D-glucopyranoside (495378-99-9)

Guidance literature:

With N-Bromosuccinimide; tetraethylammonium trifluoromethanesulphonate; trifluoroacetic acid; In dichloromethane; at -24 ℃; for 0.1h; Molecular sieve;

DOI:10.1080/00397911.2014.894526

Reference yield:

4-Methoxybenzyl alcohol (105-13-5) → methyl 2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-α-D-glucopyranoside (495378-99-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 1 h / 50 °C / Microwave irradiation; Molecular sieve

2: N-Bromosuccinimide; tetraethylammonium trifluoromethanesulphonate; trifluoroacetic acid / dichloromethane / 0.1 h / -24 °C / Molecular sieve

With N-Bromosuccinimide; tetraethylammonium trifluoromethanesulphonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In dichloromethane; toluene;

DOI:10.1080/00397911.2014.894526

upstream raw materials:

(2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-ol

p-methoxybenzyl chloride

4-methoxybenzyl N-allyl thiocarbamate

4-Methoxybenzyl alcohol

Downstream raw materials:

methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-6-O-triflyl-α-D-glucopyranoside

methyl 2,3-di-O-benzyl-6-deoxy-4-O-p-methoxybenzyl-6-C-(4'-vinyloxyazetidin-2'-on-1'-yl)-α-D-glucopyranoside

(2S,3R,4S,4aR,5aR,8aR)-3,4-dibenzyloxy-1,5-dioxa-2-methoxy-7a-azacyclobuta[b]decalin-7-one

methyl 2,3-bis-O-benzyl-4-O-[(4-methoxyphenyl)methyl]-α-D-glucopyranoside