888487-32-9

Basic information

• Product Name: 2-deoxy-1-O-dibenzylphosphoryl-2-fluoro-3,4,6,7-tetra-O-pivaloyl-L-glycero-β-D-gluco-heptopyranose
• Synonyms: 2-deoxy-1-O-dibenzylphosphoryl-2-fluoro-3,4,6,7-tetra-O-pivaloyl-L-glycero-β-D-gluco-heptopyranose
• CAS NO: 888487-32-9
• Molecular Weight: 808.876
• Mol File: 888487-32-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-deoxy-1-O-dibenzylphosphoryl-2-fluoro-3,4,6,7-tetra-O-pivaloyl-L-glycero-β-D-gluco-heptopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2-deoxy-1-O-dibenzylphosphoryl-2-fluoro-3,4,6,7-tetra-O-pivaloyl-L-glycero-β-D-gluco-heptopyranose(888487-32-9)
• EPA Substance Registry System: 2-deoxy-1-O-dibenzylphosphoryl-2-fluoro-3,4,6,7-tetra-O-pivaloyl-L-glycero-β-D-gluco-heptopyranose(888487-32-9)

Safety Data

• Hazardous Substances Data: 888487-32-9(Hazardous Substances Data)

Upstream product

• 888487-31-8 1,5-anhydro-2-deoxy-3,4,6,7-tetra-O-pivaloyl-L-galacto-hept-1-enitol 
• 97174-13-5 sodium dibenzyl phosphate 

Relevant articles and documents

β-Selective one-pot fluorophosphorylation of d,d -heptosylglycals mediated by selectfluor

This study describes the development of a novel procedure of glycal fluorophosphorylation applied to the synthesis of a fluorinated analogue of an important bacterial metabolite. This procedure was applied to several heptose-derived glycals, and the stereochemical outcome of the reaction was analyzed. Under optimized conditions, the reaction is β-gluco selective, but a significant amount of the α-gluco diastereomer is also generated.

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.