Literature DB >> 16956218

Synthesis of a beta-(1-->3)-D-rhamnotetraose by a one-pot, multiple radical fragmentation.

David Crich1, Albert A Bowers.   

Abstract

A naturally occurring beta-(1-->3)-D-rhamnotetraose has been constructed under conditions of sequential beta-selective mannosylation controlled by the 4,6-O-[1-cyano-2-(2-iodophenyl)-ethylidene] protecting group. The route is concise, proceeding through a late-stage radical deoxygenation that successfully uncovers all four deoxy subunits at once.

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Year:  2006        PMID： 16956218      PMCID： PMC2617736          DOI： 10.1021/ol061706m

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  35 in total

1.  Confirmation of the connectivity of 4,8,12,16,20-pentamethylpentacosylphoshoryl beta-D-mannopyranoside, an unusual beta-mannosyl phosphoisoprenoid from Mycobacterium avium, through synthesis.

Authors:  David Crich; Vadim Dudkin
Journal:  J Am Chem Soc       Date:  2002-03-13       Impact factor: 15.419

2.  Toward fully synthetic N-linked glycoproteins.

Authors:  Justin S Miller; Vadim Y Dudkin; Gholson J Lyon; Tom W Muir; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2003-01-27       Impact factor: 15.336

3.  Identification of the lipopolysaccharide O-chain of Escherichia hermannii (ATCC 33651) as a D-rhamnan.

Authors:  M B Perry; J C Richards
Journal:  Carbohydr Res       Date:  1990-09-19       Impact factor: 2.104

4.  Somatic antigens of the pseudomonads: structure of the O-specific polysaccharide chain of Pseudomonas syringae pv. tabaci 225 (serogroup VIII) lipopolysaccharide.

Authors:  E V Vinogradov; A S Shashkov; Y A Knirel; G M Zdorovenko; L P Solyanik; L M Yakovleva
Journal:  Carbohydr Res       Date:  1991-06-10       Impact factor: 2.104

5.  Structural elucidation of two polysaccharides present in the lipopolysaccharide of a clinical isolate of Burkholderia cepacia.

Authors:  S Cérantola; H Montrozier
Journal:  Eur J Biochem       Date:  1997-06-01

6.  Direct synthesis of beta-mannans. A hexameric [-->3)-beta-D-Man-(1](3) subunit of the antigenic polysaccharides from Leptospira biflexa and the octameric (1-->2)-linked beta-D-mannan of the Candida albicans phospholipomannan. X-ray crystal structure of a protected tetramer.

Authors:  D Crich; H Li; Q Yao; D J Wink; R D Sommer; A L Rheingold
Journal:  J Am Chem Soc       Date:  2001-06-20       Impact factor: 15.419

7.  First synthesis of the beta-D-rhamnosylated trisaccharide repeating unit of the O-antigen from Xanthomonas campestris pv. campestris 8004.

Authors:  Emiliano Bedini; Antonella Carabellese; Gaspare Barone; Michelangelo Parrilli
Journal:  J Org Chem       Date:  2005-09-30       Impact factor: 4.354

8.  Structure of the O20 antigen of Stenotrophomonas (Xanthomonas or Pseudomonas) maltophilia.

Authors:  A M Winn; S G Wilkinson
Journal:  Carbohydr Res       Date:  1996-11-20       Impact factor: 2.104

9.  Benzylidene acetal fragmentation route to 6-deoxy sugars: direct reductive cleavage in the presence of ether protecting groups, permitting the efficient, highly stereocontrolled synthesis of beta-D-rhamnosides from D-mannosyl glycosyl donors. Total synthesis of alpha-D-Gal-(1-->3)-alpha-D-Rha-(1-->3)- beta-D-Rha-(1-->4)-beta-D-Glu-OMe, the repeating unit of the antigenic lipopolysaccharide from Escherichia hermannii ATCC 33650 and 33652.

Authors:  David Crich; Qingjia Yao
Journal:  J Am Chem Soc       Date:  2004-07-07       Impact factor: 15.419

10.  Direct chemical synthesis of the beta-mannans: linear and block syntheses of the alternating beta-(1-->3)-beta-(1-->4)-mannan common to Rhodotorula glutinis, Rhodotorula mucilaginosa, and Leptospira biflexa.

Authors:  David Crich; Wenju Li; Hongmei Li
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419
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  8 in total

1.  Convergent synthesis of a beta-(1-->3)-mannohexaose.

Authors:  David Crich; Baolin Wu; Prasanna Jayalath
Journal:  J Org Chem       Date:  2007-08-01       Impact factor: 4.354

2.  Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

Authors:  David Crich
Journal:  J Org Chem       Date:  2011-10-04       Impact factor: 4.354

3.  Stereocontrolled synthesis of D- and L-beta-rhamnopyranosides with 4-O-6-S-alpha-cyanobenzylidene-protected 6-thiorhamnopyranosyl thioglycosides.

Authors:  David Crich; Linfeng Li
Journal:  J Org Chem       Date:  2009-01-16       Impact factor: 4.354

4.  Direct stereocontrolled synthesis of 3-amino-3-deoxy-beta-mannopyranosides: importance of the nitrogen protecting group on stereoselectivity.

Authors:  David Crich; Huadong Xu
Journal:  J Org Chem       Date:  2007-06-13       Impact factor: 4.354

5.  Stereocontrolled glycoside and glycosyl ester synthesis. neighboring group participation and hydrogenolysis of 3-(2'-benzyloxyphenyl)-3,3-dimethylpropanoates.

Authors:  David Crich; Feng Cai
Journal:  Org Lett       Date:  2007-03-09       Impact factor: 6.005

6.  En Route to the Transformation of Glycoscience: A Chemist's Perspective on Internal and External Crossroads in Glycochemistry.

Authors:  David Crich
Journal:  J Am Chem Soc       Date:  2020-12-22       Impact factor: 15.419

Review 7.  Protecting groups in carbohydrate chemistry: influence on stereoselectivity of glycosylations.

Authors:  Jian Guo; Xin-Shan Ye
Journal:  Molecules       Date:  2010-10-20       Impact factor: 4.411

8.  Efficient routes toward the synthesis of the D-rhamno-trisaccharide related to the A-band polysaccharide of Pseudomonas aeruginosa.

Authors:  Aritra Chaudhury; Sajal K Maity; Rina Ghosh
Journal:  Beilstein J Org Chem       Date:  2014-07-01       Impact factor: 2.883
  8 in total

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