Literature DB >> 12668091

The synthesis of gracillin and dioscin: two typical representatives of spirostanol glycosides.

Chuan-Chun Zou1, Shu-Jie Hou, Yang Shi, Ping-Sheng Lei, Xiao-Tian Liang.   

Abstract

Two representative spirostanol saponins that have the typical structure for the sugar moiety, diosgenyl alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside (gracillin) and diosgenyl alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside (dioscin), were easily synthesized by a general approach. A procedure using guanidine for the selective deblocking of acetyl while retaining benzoyl protecting groups is described.

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Year:  2003        PMID: 12668091     DOI: 10.1016/s0008-6215(03)00004-1

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN: 0008-6215            Impact factor:   2.104


  4 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.  Anthelmintic activity of steroidal saponins from Dioscorea zingiberensis C. H. Wright against Dactylogyrus intermedius (Monogenea) in goldfish (Carassius auratus).

Authors:  Gao-Xue Wang; Dong-Xin Jiang; Jun Li; Jing Han; You-Tao Liu; Xiao-Lin Liu
Journal:  Parasitol Res       Date:  2010-08-06       Impact factor: 2.289

3.  Two spirostan steroid glycoside fatty esters from Dioscorea cayenensis.

Authors:  Zulfiqar Ali; Troy J Smillie; Ikhlas A Khan
Journal:  Nat Prod Commun       Date:  2013-03       Impact factor: 0.986

4.  N-Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity.

Authors:  Agata Walczewska; Daria Grzywacz; Dorota Bednarczyk; Małgorzata Dawgul; Andrzej Nowacki; Wojciech Kamysz; Beata Liberek; Henryk Myszka
Journal:  Beilstein J Org Chem       Date:  2015-05-22       Impact factor: 2.883

  4 in total

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