40246-27-3

Basic information

• Product Name: 3,4,6-tri-O-benzyl-1,2-O-methoxybenzylidene-α-D-glucopyranose
• Synonyms: 3,4,6-tri-O-benzyl-1,2-O-methoxybenzylidene-α-D-glucopyranose
• CAS NO: 40246-27-3
• Molecular Weight: 658.748
• Mol File: 40246-27-3.mol

Chemical Properties

• CAS DataBase Reference: 3,4,6-tri-O-benzyl-1,2-O-methoxybenzylidene-α-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,6-tri-O-benzyl-1,2-O-methoxybenzylidene-α-D-glucopyranose(40246-27-3)
• EPA Substance Registry System: 3,4,6-tri-O-benzyl-1,2-O-methoxybenzylidene-α-D-glucopyranose(40246-27-3)

Safety Data

• Hazardous Substances Data: 40246-27-3(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 

Downstream Products

• 68536-62-9 Benzoic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-cyclohexyloxy-tetrahydro-pyran-3-yl ester 
• 68536-62-9 2-O-benzoyl-1-O-cyclohexyl-3,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 68536-61-8 Benzoic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-isobutoxy-tetrahydro-pyran-3-yl ester 
• 73445-33-7 Benzoic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-isobutoxy-tetrahydro-pyran-3-yl ester 
• 40246-29-5 Benzoic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl ester 
• 73445-32-6 methyl 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 73445-27-9 methyl 3,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 73445-29-1 methyl 2-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 73445-36-0 methyl 2-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-3,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 73445-30-4 methyl 3,4,6-tri-O-benzyl-2-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-galactopyranoside 
• 68536-60-7 Benzoic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-{2-[4-(toluene-4-sulfonylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yl ester 
• 73445-34-8 Benzoic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-{2-[4-(toluene-4-sulfonylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yl ester 
• 73494-51-6 Benzoic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(toluene-4-sulfonyloxy)-tetrahydro-pyran-3-yl ester 
• 73445-28-0 methyl 6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2,3,4-tri-O-benzyl-α-D-galactopyranoside 

Relevant articles and documents

An expeditious route to Streptococci and Enterococci glycolipids via ring-opening of 1,2-anhydrosugars with protic acids

1,2-Anhydroglucose 6 reacts smoothly and with a high degree of stereoselectivity with a variety of carboxylic and phosphoric acids resulting in the formation of the predominantly β-oriented 1-O-acyl and 1-O-phosphorylglucoses 7-17. This methodology has been successfully applied in the construction of glycolipids 1a,b. Ring-opening of the 1,2-anhydroglucose derivative 19 with benzoic acid furnished exclusively the β-aligned key intermediate 20. Subsequent ICDT-assisted chemoselective α-glucosylation of 20 with thioethyl donor 21, followed by glycosidation of kojibiosyl benzoate 22 with glycerol acceptor 23 gave the fully protected α-diglucosyl glycerol derivative 25, which upon desilylation (→28), acylation (→29 or 30) and deprotection afforded the target glycolipids 1a-b in high overall yield.