Literature DB >> 15471500

Stereospecific uncatalyzed alpha-O-glycosylation and alpha-C-glycosidation by means of a new D-Gulal-derived alpha vinyl oxirane.

Valeria Di Bussolo1, Micaela Caselli, Maria Rosaria Romano, Mauro Pineschi, Paolo Crotti.   

Abstract

The reaction of alpha vinyl oxirane 5, prepared through a new route to the d-gulal system, with O-nucleophiles (alcohols and di-O-isopropylidene-alpha-d-monosaccharides) and C-nucleophiles (lithium alkyls) affords, in a completely stereoselective way, the corresponding 2-unsaturated alpha O- and C-glycosides having the same configuration as the starting epoxide.

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Year:  2004        PMID: 15471500     DOI: 10.1021/jo0491152

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  3 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

Review 2.  Chemical O-Glycosylations: An Overview.

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

3.  The convergent total synthesis and antibacterial profile of the natural product streptothricin F.

Authors:  Matthew G Dowgiallo; Brandon C Miller; Mintesinot Kassu; Kenneth P Smith; Andrew D Fetigan; Jason J Guo; James E Kirby; Roman Manetsch
Journal:  Chem Sci       Date:  2022-02-25       Impact factor: 9.969

  3 in total

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