208656-41-1

Upstream product

• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 107-66-4 dibutyl phosphate 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 

Downstream Products

• 331281-73-3 Dibutyl 3,4,6-tri-O-benzyl-2-O-para-chlorophenylcarbonyl-β-D-glucipyranosyl phosphate 
• 40246-33-1 3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 
• 331281-75-5 3,4,6-Tri-O-benzyl-2-para-chlorophenylcarbonyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-diisopropylidene-α-D-galactopyranoside 
• 208656-42-2 dibutyl (2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl) phosphate 

Relevant academic research and scientific papers

para-Chlorophenyl carbonate as a versatile hydroxyl protecting group

The p-chlorophenyl carbonate (CPC) group can be readily applied and rapidly removed in the presence of various protecting groups including pivaloyl and benzoyl esters. Additionally, the CPC group is stable under a variety of glycosylation conditions and yields solely β-linked glycosides when used as a C2 participating group.

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.