Literature DB >> 14685319

A novel strategy towards the synthesis of orthogonally functionalised 4-aminoglycosides.

Leendert J van den Bos1, Jeroen D C Codée, Jacques H van Boom, Herman S Overkleeft, Gijsbert A van der Marel.   

Abstract

A tethered nucleophilic substitution strategy for the stereoselective introduction of axially oriented amino functions on suitably protected gluco- and mannopyranosides is presented. The obtained oxazine is a versatile building block, which after some manipulation, could be used in the construction of highly functionalised oligosaccharides.

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Year:  2003        PMID： 14685319     DOI： 10.1039/b309823k

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  3 in total

1.  Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl- (1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-(1-->4)-alpha-L- rhamno-pyranoside, a tetrasaccharide subunit of the lipopolysaccharide from Plesimonas shigelloides.

Authors:  David Crich; Abhisek Banerjee
Journal:  J Am Chem Soc       Date:  2006-06-21       Impact factor: 15.419

2.  Electrochemical generation of glycosyl triflate pools.

Authors:  Toshiki Nokami; Akito Shibuya; Hiroaki Tsuyama; Seiji Suga; Albert A Bowers; David Crich; Jun-ichi Yoshida
Journal:  J Am Chem Soc       Date:  2007-08-14       Impact factor: 15.419

3.  Synthesis of 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-manno derivatives as versatile building blocks.

Authors:  Catherine Alex; Satsawat Visansirikul; Yongzhen Zhang; Jagodige P Yasomanee; Jeroen Codee; Alexei V Demchenko
Journal:  Carbohydr Res       Date:  2019-12-23       Impact factor: 2.104
  3 in total

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