255894-68-9

Upstream product

• 545-06-2 trichloroacetonitrile 
• 242473-77-4 allyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 113893-72-4 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 
• 136737-75-2 allyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 64650-81-3 allyl α-L-rhamnopyranoside 
• 89202-38-0 2,3,4-Tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranose 
• 1053351-01-1 allyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl(1->3)-α-L-rhamnopyranoside 

Downstream Products

• 402913-30-8 methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-D-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 287203-85-4 Ethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-O-acetyl-4-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-O-acetyl-4-O-benzoyl-1-thio-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

Synthesis of an L-rhamnose tetrasaccharide, the common and major structure of the repeating unit of the O-antigenic polysaccharide of a strain of Klebsiella pneumoniae and Pseudomonas holci

A tetrasaccharide, α-L-Rhap-(1 → 3)-α-L-Rhap-(1 → 2)-α-L-Rhap-(1 → 2)-L-Rhap, the common and major structure of the repeating unit of the O-antigenic polysaccharide of a strain of Klebsiella pneumoniae and Pseudomonas holci was synthesized as its methyl and octyl glycosides. Selective 3-O-glycosylation of allyl α-L-rhamnopyranoside with 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl trichloroacetimidate gave allyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1 → 3)-α-L-rhamnopyranoside (3). Benzoylation, deallylation, and trichloroacetimidation afforded 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1 → 3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate (6). Self condensation of 3,4-di-O-benzoyl-β-L-rhamnopyranose 1,2-methyl orthoester or 1,2-octyl orthoester gave methyl or octyl 2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1 → 2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside (16 or 17), and subsequent selective deacetylation gave the disaccharide acceptor (18 or 19). Coupling of 6 with 18 (or 19), followed by deacylation in ammonia-saturated methanol, produced the target tetrasacharide.

Synthesis of a group of diosgenyl saponins with combined use of glycosyl trichloroacetimidate and thioglycoside donors

With the combined use of glycosyl trichloroacetimidates and thioglycosides, a group of natural diosgenyl saponins (1-6) are efficiently synthesized, in either a stepwise or a 'one-pot' manner. The trichloroacetimidate is employed as an efficient temporary hydroxy protecting group in glycosylation with the glycosyl trichloroacetimidate. The intermolecular alkylthio-group transfer is demonstrated to be a common side-reaction during glycosylation with thioglycosides. The Royal Society of Chemistry 2000.

Synthesis of a group of diosgenyl saponins by a one-pot sequential glycosylation

A group of natural diosgenyl saponins was synthesized in a highly efficient manner employing the 'one-pot sequential glycosylation' protocol with the combined use of glycosyl trichloroacetimidates and thioglycosides.