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Org Lett. 2018 Oct 05;20(19):6051-6054. doi: 10.1021/acs.orglett.8b02424. Epub 2018 Sep 14.

A Ring Contraction of 2,3-Di- O-Silylated Thiopyranosides To Give Thiofuranosides under Mildly Acidic Conditions.

Organic letters

Polina I Abronina, Nelly N Malysheva, Veronika V Litvinenko, Alexander I Zinin, Natalya G Kolotyrkina, Leonid O Kononov

Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences , Leninsky prosp., 47 , Moscow 119991 , Russian Federation.

PMID: 30216074 DOI: 10.1021/acs.orglett.8b02424

Abstract

A pyranose ring contraction of ethyl 1-thio-β-d-galactopyranosides has been discovered that proceeds with retention of aglycon under mildly acidic conditions (aq TFA in CH

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