158923-64-9

Upstream product

• 64-19-7 acetic acid 
• 1011723-04-8 glucal epoxide 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 53270-12-5 1,2-O-(1-ethoxyethylene) 3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranose 
• 3254-17-9 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-glucopyranose 
• 100-39-0 benzyl bromide 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 

Downstream Products

• 205502-40-5 (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(1-ethoxy-ethoxy)-tetrahydro-pyran-2-ol 
• 205502-42-7 (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-isopropenyl-tetrahydro-pyran-3-ol 
• 205502-41-6 3,4,6-tri-O-benzyl-D-glucono-1,5-lactone 

Relevant academic research and scientific papers

Synthesis of 3-O-(β-d-xylopyranosyl-(1→2)-β-d-glucopyranosyl)-3′-O-(β-d-glucopyranosyl)tamarixetin, the putative structure of aescuflavoside A from the seeds of Aesculus chinensis

3-O-(β-d-Xylopyranosyl-(1→2)-β-d-glucopyranosyl)-3′-O-(β-d-glucopyranosyl)tamarixetin, the putative flavonal glycoside named aescuflavoside A, isolated from the seeds of Aesculus chinensis, is synthesized via regioselective glycosylation of 7-O-benzyltama

Highly stereoselective hydroformylation of olefins possessing chiral sugar templates

Hydroformylation of 1,1-disubstituted olefins possessing chiral sugar templates gave β-substituted aldehydes in good to excellent yields with up to 99% diastereoselectivity.

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.