888487-37-4

Upstream product

• 108-24-7 acetic anhydride 
• 155020-90-9 methyl 2,3,4-tri-O-benzyl-7-O-tert-butyldimethylsilyl-D-glycero-α-D-gluco-heptopyranoside 
• 127214-37-3 (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran 
• 103597-20-2 methyl 2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside 
• 177897-27-7 (S)-Hydroxy-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetaldehyde 
• 117192-23-1 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-C--α-D-xylofuranose 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 83051-88-1 methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 177897-24-4 (E)-(R)-4-Acetoxy-4-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-but-2-enoic acid methyl ester 
• 177897-23-3 Acetic acid (S)-2-oxo-1-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl ester 

Relevant academic research and scientific papers

METHODS FOR PREPARING ENZYMATIC SUBSTRATE ANALOGS USEFUL AS INHIBITORS OF BACTERIAL HEPTOSYL-TRANSFERASES AND BIOLOGICAL APPLICATIONS OF THE INHIBITORS

The invention relates to a method for making osyl and hexoses derivatives of formula (1), especially 2-fluoro-2-deoxy derivatives, wherein R is a nucleoside such as adenosine, cytidine, guanosine, uridine and deoxy analogs such as 2-deoxy, X represents OH, halogen, particularly F, NH2, Y represents H, CH2OH, CH2NH2, CH2OPO3, CH2OSO3, Z represents O or S, and W represents O,NH, or CH2, said method comprising the steps of: a) stereoselective fluorophosphorylation of tetrapivaleate 8 to give β-gluco-type fluorophosphate, b) hydrogenation and deprotection to give a monophosphate, c) coupling said glycal with (R)P-morpholidate to give crude sugar nucleotide 1, or . alternatively, d)deacetylation then silylation of heptoglycal 7 to give tetrasilylated glycal, e)fluorophosphorylation of said glycal to give β-gluco type fluorophosphate, f) deprotection of the fluorophosphate and coupling radical R to give 1. Use of said derivatives as inhibitors of highly virulent proteins of pathogenic bacteria.

Preparation of sugar-derived α-acetoxy-aldehydes

A convenient method for conversion of sugar diols (2a-2d) into a-acetoxy-aldehydes: 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranos-6-ulose (5a), 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranos-6-ulose (5b), methyl 6-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco- and L-glycero-α-D-gluco-heptopyranosid-7-uloses (5c and 5d respectively) is presented. This involves the protection (as TBDMS ether) of the primary hydroxyl group, acetylation of the remaining secondary one and desilylation followed by a Swern oxidation. Partial migration of the acetyl group during desilylation (with Bu4NF) was observed for compound 4a and complete migration for 4f. α-Acetoxy-aldehydes 5a-5d were characterized as adducts with Ph3P = CH-CO2Me (12a-12d).