Literature DB >> 12375921

New stereoselective beta-glycosylation via a vinyl oxirane derived from D-glucal.

Valeria Di Bussolo1, Micaela Caselli, Mauro Pineschi, Paolo Crotti.   

Abstract

[reaction: see text] The reaction of the vinyl oxirane 1 derived from D-glucal with a series of O-nucleophiles (alcohols, phenol, and diacetone D-glucose) affords the corresponding 2-unsaturated beta-O-glycosides in a completely stereoselective way (syn 1,4-addition pathway). Epoxide 1 is generated in situ by treatment of the corresponding hydroxy mesylate 2 with t-BuOK in anhydrous benzene.

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Year:  2002        PMID： 12375921     DOI： 10.1021/ol026648t

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  4 in total

1.  Synthesis and biological evaluation of non-glucose glycoconjugated N-hydroyxindole class LDH inhibitors as anticancer agents.

Authors:  Valeria Di Bussolo; Emilia C Calvaresi; Carlotta Granchi; Linda Del Bino; Ileana Frau; Maria Chiara Dasso Lang; Tiziano Tuccinardi; Marco Macchia; Adriano Martinelli; Paul J Hergenrother; Filippo Minutolo
Journal:  RSC Adv       Date:  2015       Impact factor: 3.361

2.  (-)-Benzyl 2,3-dide-oxy-β-d-erythro-hex-2-eno-pyran-oside.

Authors:  Shigeru Ohba; Hayato Okazaki; Yuji Ueda; Kengo Hanaya; Mitsuru Shoji; Takeshi Sugai
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-11-23

Review 3.  Chemical O-Glycosylations: An Overview.

Authors:  Rituparna Das; Balaram Mukhopadhyay
Journal:  ChemistryOpen       Date:  2016-08-17       Impact factor: 2.911

4.  Aziridine Ring Opening as Regio- and Stereoselective Access to C-Glycosyl-Aminoethyl Sulfide Derivatives.

Authors:  Aleksandra Tracz; Martyna Malinowska; Stanisław Leśniak; Anna Zawisza
Journal:  Molecules       Date:  2022-03-08       Impact factor: 4.411
  4 in total

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