Literature DB >> 18243266

Synthesis of "glycospirostanes"--steroid sapogenins with a sugar-like ring F.

Yliana López1, Izabella Jastrzebska, Rosa Santillan, Jacek W Morzycki.   

Abstract

The synthesis of two "glycospirostanes" from 23-oxotigogenin acetate is described. (23S,24S,25R)-5alpha-Spirostane-3beta,23,24,25-tetraol was obtained by dehydrogenation followed by stereoselective reduction of the 23-oxo group and OsO(4) dihydroxylation of the C24-C25 double bond. Allylic hydroxylation with SeO(2) of 3beta-acetoxy-5alpha-spirost-23-ene obtained from 23-oxotigogenin acetate followed by OsO(4) dihydroxylation of the C23-C24 double bond afforded (23R,24S,25R)-5alpha-spirostane-3beta,23,24,25-tetraol.

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Year:  2008        PMID: 18243266     DOI: 10.1016/j.steroids.2007.12.015

Source DB:  PubMed          Journal:  Steroids        ISSN: 0039-128X            Impact factor:   2.668


  2 in total

1.  Synthesis and antifungal activity of functionalized 2,3-spirostane isomers.

Authors:  Sunil Kumar Upadhyay; Clinton C Creech; Katharine L Bowdy; Edwin D Stevens; Branko S Jursic; Donna M Neumann
Journal:  Bioorg Med Chem Lett       Date:  2011-03-30       Impact factor: 2.823

2.  A Convenient Synthesis of (16S,20S)-3β-hydroxy-5α-pregnane-20,16-carbolactam and its N-alkyl Derivatives.

Authors:  Agnieszka Wojtkielewicz; Damian Pawelski; Przemysław Bazydło; Aneta Baj; Stanisław Witkowski; Jacek W Morzycki
Journal:  Molecules       Date:  2020-05-20       Impact factor: 4.411

  2 in total

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