Premium
Stereocontrolled Synthesis of 2‐Fluorinated C ‐Glycosides
Author(s) -
Sadurní Anna,
Gilmour Ryan
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800618
Subject(s) - chemistry , substituent , nucleophile , stereochemistry , glycoside , nuclear magnetic resonance spectroscopy , organic chemistry , catalysis
A systematic study of the addition of C ‐based nucleophiles to fluorinated lactones based on 2‐deoxy‐2‐fluoro‐ d ‐pyranoses is disclosed. This high yielding, α‐selective process was found to be independent on the nature or configuration [( R )‐C(sp 3 )–F, ( S )‐C(sp 3 )–F] of the substituent at C2 . Representative, fluorinated analogues of Trehalose, Carminic acid, and the spirocyclic cores of Tofogliflozin and Papulacandin D are also reported. These glycomimics constitute a valuable series of 19 F NMR active probes for application in structural biology.