850648-03-2

Upstream product

• 850647-87-9 phenyl 2,3-di-O-benzyl-6,7-dideoxy-4-O-(p-methoxybenzyl)-α-D-thiohept-6-enopyranoside 
• 850647-86-8 phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside 
• 850647-89-1 phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-D-glycero-α-D-thio-manno-heptopyranoside 
• 808762-01-8 phenyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 850647-91-5 phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-6-O-(p-nitrobenzoyl)-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-thiomannoheptopyranoside 
• 850647-94-8 phenyl 2,3-di-O-benzyl-4,6-O-(p-methoxybenzylidene)-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-thiomannoheptopyranoside 
• 850647-92-6 phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-thiomannoheptopyranoside 
• 850647-90-4 phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-L-glycero-α-D-thio-manno-heptopyranoside 
• 850647-96-0 methyl 2,3-di-O-benzyl-4,6-O-(p-methoxybenzylidene)-7-O-(t-butyldiphenylsilyl)-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Stereocontrolled synthesis of the D- and L-glycero-β-D-manno- heptopyranosides and their 6-deoxy analogues. Synthesis of methyl α-L-rhamno-pyranosyl-(1→3)-D-glycero-β-D-manno-heptopyranosyl- (1→3)-6-deoxy-glycero-β-D-manno-heptopyranosyl-(1→4) -α-L-rhamno-pyranoside, a tetrasaccharide subunit of the lipopolysaccharide from Plesimonas shigelloides

The synthesis of D- and L-glycero-α-manno-thioheptopyranosides, protected with 4,6-O-alkylidene-type acetals is described. In glycosylations carried out with preactivation with the 1-benzenesulfinylpiperidine/ trifluoromethanesulfonic anhydride couple, both the D- and L-glycero series exhibit excellent β-selectivity with a range of glycosyl acceptors. In contrast, a 4,7-O-alkylidene acetal was found not to afford β-selectivity. With a 4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene] acetal protected thioglycoside, excellent β-selectivity was obtained in glycosylation reactions, and subsequent treatment with tributyltin hydride and azoisobutyronitrile brought about clean fragmentation to the 6-deoxy-glycero-β-D-manno-heptopyranosides. This chemistry was applied to the stereocontrolled synthesis of methyl α-L-rhamnopyranosyl-(1→3)-D- glycero-β-D-manno-heptopyranosyl-(1→3)-6-deoxy-glycero-β-D-manno- heptopyranosyl-(1→4)-α-L-rhamno-pyranoside, a component of the lipopolysaccharide from Plesimonas shigelloides.

Synthesis and stereoselective glycosylation of D- and L-glycero-β-D- manno-heptopyranoses

(Chemical Equation Presented) A method for the direct stereocontrolled synthesis of D- and L-glycero-β-D-manno-heptopyranosides such as those found in the repeating unit of the O-specific polysaccharide from the CNCTC 113/92 LPS (serotype 54) is described