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Stereocontrolled Synthesis of 2-Fluorinated C-Glycosides.

ABSTRACT: 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, ?-selective process was found to be independent on the nature or configuration [(R)-C(sp³)-F, (S)-C(sp³)-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 ¹⁹F NMR active probes for application in structural biology.

SUBMITTER: Sadurni A

PROVIDER: S-EPMC6099233 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Stereocontrolled Synthesis of 2-Fluorinated C-Glycosides.

Sadurní Anna A Gilmour Ryan R

European journal of organic chemistry 20180607 27-28

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(sp3)-F, (S)-C(sp3)-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 glycomi ...[more]

PMID: 30147438

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