Access to n-pentenyl tetra- and pentasaccharide analogues of the antitumor drug PI-88 based on 1,2-methyl orthoester glycosyl donors

Convergent synthetic routes to PI-88 tetra- and pentasaccharide-component analogues, have been developed featuring regioselective glycosylations of mannose-polyol n-pentenyl glycosides (NPG) acceptors with 1,2-methyl orthoesters (MeOE) glycosyl donors. [Display omitted] •Convergent synthetic approac...

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Bibliographic Details
Published in:Carbohydrate research 2022-06, Vol.516, p.108557-108557, Article 108557
Main Authors: Ventura, Juan, Uriel, Clara, Gómez, Ana M., López, J. Cristobal
Format: Article
Language:English
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Summary:Convergent synthetic routes to PI-88 tetra- and pentasaccharide-component analogues, have been developed featuring regioselective glycosylations of mannose-polyol n-pentenyl glycosides (NPG) acceptors with 1,2-methyl orthoesters (MeOE) glycosyl donors. [Display omitted] •Convergent synthetic approaches to saccharide analogues of antitumor drug PI-88.•1,2-Methyl orthobenzoates (MeOE) were used exclusively as glycosyl donors.•An n-pentenyl glycoside was incorporated at the reducing-end of the PI-88 analogues.•Regioselective glycosyl coupling of D-mannose-derived polyols minimizes protecting group manipulations.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2022.108557