208656-40-0

Basic information

• Product Name: Phosphoric acid dibenzyl ester (2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl ester
• CAS NO: 208656-40-0
• Molecular Weight: 710.761
• Mol File: 208656-40-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Phosphoric acid dibenzyl ester (2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphoric acid dibenzyl ester (2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl ester(208656-40-0)
• EPA Substance Registry System: Phosphoric acid dibenzyl ester (2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl ester(208656-40-0)

Safety Data

• Hazardous Substances Data: 208656-40-0(Hazardous Substances Data)

Upstream product

• 1623-08-1 phosphoric acid dibenzyl ester 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 

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.