Literature DB >> 22054226

Assembly of digitoxin by gold(I)-catalyzed glycosidation of glycosyl o-alkynylbenzoates.

Yuyong Ma1, Zhongzhen Li, Hefang Shi, Jian Zhang, Biao Yu.   

Abstract

Digitoxin, a clinically important cardiac trisaccharide, was assembled efficiently from digitoxigenin and 3,4-di-O-tert-butyldiphenylsilyl-d-digitoxosyl o-cyclopropylethynylbenzoate in 9 steps and 52% overall yield via alternate glycosylation and protecting group manipulation. The present synthesis showcases the advantage of the gold(I)-catalyzed glycosylation protocol in the synthesis of glycoconjugates containing acid-labile 2-deoxysugar linkages.
© 2011 American Chemical Society

Entities:  

Mesh：

Substances：

Year:  2011        PMID： 22054226     DOI： 10.1021/jo201850z

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


  10 in total

Review 1.  Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Authors:  Matteo Panza; Salvatore G Pistorio; Keith J Stine; Alexei V Demchenko
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

2.  Recent Advances in Transition Metal-Catalyzed Glycosylation.

Authors:  Matthew J McKay; Hien M Nguyen
Journal:  ACS Catal       Date:  2012-06-14       Impact factor: 13.084

Review 3.  Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.

Authors:  Yashapal Singh; Scott A Geringer; Alexei V Demchenko
Journal:  Chem Rev       Date:  2022-06-08       Impact factor: 72.087

4.  Highly reactive 2-deoxy-2-iodo-d-allo and d-gulo pyranosyl sulfoxide donors ensure β-stereoselective glycosylations with steroidal aglycones.

Authors:  Jordi Mestre; David Collado; David Benito-Alifonso; Miguel A Rodríguez; M Isabel Matheu; Yolanda Díaz; Sergio Castillón; Omar Boutureira
Journal:  RSC Adv       Date:  2018-08-24       Impact factor: 4.036

5.  Silver-catalyzed stereoselective formation of glycosides using glycosyl ynenoates as donors.

Authors:  Xu Dong; Li Chen; Zhitong Zheng; Xu Ma; Zaigang Luo; Liming Zhang
Journal:  Chem Commun (Camb)       Date:  2018-07-18       Impact factor: 6.222

6.  Total synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects.

Authors:  Xiaheng Zhang; Yu Zhou; Jianping Zuo; Biao Yu
Journal:  Nat Commun       Date:  2015-01-20       Impact factor: 14.919

7.  Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry.

Authors:  Swati S Nigudkar; Alexei V Demchenko
Journal:  Chem Sci       Date:  2015-05-01       Impact factor: 9.825

Review 8.  Chemical O-Glycosylations: An Overview.

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

9.  Doxorubicin and Aclarubicin: Shuffling Anthracycline Glycans for Improved Anticancer Agents.

Authors:  Dennis P A Wander; Sabina Y van der Zanden; Gijsbert A van der Marel; Herman S Overkleeft; Jacques Neefjes; Jeroen D C Codée
Journal:  J Med Chem       Date:  2020-10-16       Impact factor: 7.446

10.  Synthetic (N,N-Dimethyl)doxorubicin Glycosyl Diastereomers to Dissect Modes of Action of Anthracycline Anticancer Drugs.

Authors:  Dennis P A Wander; Sabina Y van der Zanden; Merijn B L Vriends; Branca C van Veen; Joey G C Vlaming; Thomas Bruyning; Thomas Hansen; Gijsbert A van der Marel; Herman S Overkleeft; Jacques J C Neefjes; Jeroen D C Codée
Journal:  J Org Chem       Date:  2021-03-30       Impact factor: 4.354
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.