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A Glycal Approach to the Synthesis of Pregnane Glycoside P57
Author(s) -
Liu Chao,
Ma Yuyong,
Pei Chengfeng,
Li Wei,
Yu Biao
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201800331
Subject(s) - chemistry , glycal , trisaccharide , pregnane , glycosylation , stereochemistry , stereoselectivity , glycosidic bond , glycoside , aglycone , combinatorial chemistry , organic chemistry , biochemistry , enzyme , catalysis
Pregnane glycoside P57 is known as an active component of Hoodia gordonii , which has long been used as a diet with appetite suppressant property. Chemical synthesis of P57 demands installation of β‐cymarosyl linkage onto the steroid aglycone. The stereoselective formation of this special 2‐deoxy‐β‐glycosidic linkage has previously been proven to be difficult and thus a limiting step in the synthesis of P57 and its congeners. Herein, we report the glycosylation reactions with glycals as donors and TPHB (triphenylphosphine hydrobromide) as promoter and a convergent synthesis of P57 via a β‐selective glycosylation with a trisaccharide glycal donor.