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β‐Selective One‐Pot Fluorophosphorylation of d,d ‐Heptosylglycals Mediated by Selectfluor
Author(s) -
Vincent Stéphane P.,
Tikad Abdellatif
Publication year - 2015
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.201400148
Subject(s) - chemistry , selectfluor , diastereomer , glycal , metabolite , combinatorial chemistry , heptose , stereochemistry , organic chemistry , reagent , biochemistry , stereoselectivity , catalysis , gene , mutant
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.