20771-10-2

Basic information

• Product Name: 1-O-methyl-2,3,4-tri-O-trimethylsilyl-β-D-glucopyranoside
• Synonyms: 1-O-methyl-2,3,4-tri-O-trimethylsilyl-β-D-glucopyranoside
• CAS NO: 20771-10-2
• Molecular Weight: 410.731
• Mol File: 20771-10-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-O-methyl-2,3,4-tri-O-trimethylsilyl-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-methyl-2,3,4-tri-O-trimethylsilyl-β-D-glucopyranoside(20771-10-2)
• EPA Substance Registry System: 1-O-methyl-2,3,4-tri-O-trimethylsilyl-β-D-glucopyranoside(20771-10-2)

Safety Data

• Hazardous Substances Data: 20771-10-2(Hazardous Substances Data)

Upstream product

• 180998-03-2 Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester 

Downstream Products

• 85716-44-5 methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside 
• 316172-35-7 2,3,4-tri-O-benzyl-1,6-anhydro-β-L-idopyranos-5-ulo-5-hydrate 
• 316172-37-9 2,3,4-tri-O-benzyl-5-O-methyl-1,6-anhydro-β-L-idopyranos-5-ulose 
• 316172-40-4 2,3,4-tri-O-benzyl-5-O-tert-butyldimethylsilyl-1,6-anhydro-β-L-idopyranos-5-ulose 
• 439614-74-1 (3S,5S,6R,7R,8S)-6,7,8-Tris-benzyloxy-5-methoxy-1,4-dioxa-spiro[2.5]octane 
• 439614-80-9 1-O-(2-bromobenzoyl)-2,3,4-tri-O-benzyl-β-D-xylohexoseptanosid-5-ulose 
• 6217-21-6 methyl 2,3,4-tri-O-acetyl-6-desoxy-α-D-xylo-hex-5-enopyranoside 
• 1222854-41-2 1-O-methyl-6-O-[(3S)-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)-2-methylenebutanoyl]-2,3,4-tri-O-trimethylsilyl-α-D-glucopyranose 
• 1222854-62-7 1-O-methyl-6-O-[(3R)-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)-2-methylenebutanoyl]-2,3,4-tri-O-trimethylsilyl-α-D-glucopyranose 

Relevant articles and documents

Synthesis of Methyl 6-Deoxy-6-diphenylphosphino-α-D-glucopyranoside: Temperature-Dependence of the Primary O-Tosyl Cleavage Mode

Methyl α-D-glucopyranoside is converted to methyl 6-p-toluenesulfonyl-2,3,4-tris-O-trimethylsilyl-α-D-glucopyranoside 2 and then reacted with lithium diphenylphosphide in THF. When the reaction is carried out at room temperature and below, S-O cleavage dominates giving methyl 2,3,4-tris-O-trimethylsilyl-α-D-glucopyranoside 3, whereas at 60°C in THF or at 35°C in diethyl ether, C-O cleavage occurs yielding the title carbohydrate-phosphine 4 in good yield after deprotection.