Literature DB >> 17665957

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

David Crich1, Baolin Wu, Prasanna Jayalath.   

Abstract

An as yet unknown beta-(1-->3)-mannohexaose has been synthesized by a block route involving the coupling of two trisaccharides. Comparison of three closely related attempted mannohexaose syntheses reinforces the influence of subtle matching and/or mismatching interactions on the outcome of convergent oligosaccharide synthesis.

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Year:  2007        PMID： 17665957      PMCID： PMC2617735          DOI： 10.1021/jo071009n

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


  32 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.  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

3.  The total synthesis of moenomycin A.

Authors:  James G Taylor; Xuechen Li; Markus Oberthür; Wenjiang Zhu; Daniel E Kahne
Journal:  J Am Chem Soc       Date:  2006-11-29       Impact factor: 15.419

4.  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

5.  Synthetic analogues of beta-1,2 oligomannosides prevent intestinal colonization by the pathogenic yeast Candida albicans.

Authors:  Françoise Dromer; Reynald Chevalier; Boualem Sendid; Luce Improvisi; Thierry Jouault; Raymond Robert; Jean Maurice Mallet; Daniel Poulain
Journal:  Antimicrob Agents Chemother       Date:  2002-12       Impact factor: 5.191

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

Authors:  David Crich; Albert A Bowers
Journal:  Org Lett       Date:  2006-09-14       Impact factor: 6.005

7.  IMPROVED SYNTHESIS OF 1-BENZENESULFINYL PIPERIDINE AND ANALOGS FOR THE ACTIVATION OF THIOGLYCOSIDES IN CONJUNCTION WITH TRIFLUOROMETHANESULFONIC ANHYDRIDE.

Authors:  David Crich; Abhisek Banerjee; Wenju Li; Qingjia Yao
Journal:  J Carbohydr Chem       Date:  2005       Impact factor: 1.667

8.  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

9.  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

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.  Synthesis and structural verification of the xylomannan antifreeze substance from the freeze-tolerant Alaskan beetle Upis ceramboides.

Authors:  David Crich; Md Yeajur Rahaman
Journal:  J Org Chem       Date:  2011-10-07       Impact factor: 4.354

Review 2.  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

3.  Novel galactosyl donor with 2-naphthylmethyl (NAP) as the non participating group at C-2 position: Efficient synthesis of alpha-galactosyl ceramide.

Authors:  Sirajud D Khaja; Vipin Kumar; Misbah Ahmad; Jun Xue; Khushi L Matta
Journal:  Tetrahedron Lett       Date:  2010-08-18       Impact factor: 2.415

4.  Manual and Automated Syntheses of the N-Linked Glycoprotein Core Glycans.

Authors:  Salvatore G Pistorio; Scott A Geringer; Keith J Stine; Alexei V Demchenko
Journal:  J Org Chem       Date:  2019-05-17       Impact factor: 4.354

5.  Application of the 4-trifluoromethylbenzenepropargyl ether group as an unhindered, electron deficient protecting group for stereoselective glycosylation.

Authors:  David Crich; Maheswaran S Karatholuvhu
Journal:  J Org Chem       Date:  2008-06-05       Impact factor: 4.354

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

7.  Synthetic Neoglycoconjugates of Hepta- and Nonamannoside Ligands for Eliciting Oligomannose-Specific HIV-1-Neutralizing Antibodies.

Authors:  Matteo Cattin; Jean-François Bruxelle; Kurtis Ng; Markus Blaukopf; Ralph Pantophlet; Paul Kosma
Journal:  Chembiochem       Date:  2022-02-11       Impact factor: 3.461

8.  Synthesis and reactivity of 4'-deoxypentenosyl disaccharides.

Authors:  Panuwat Padungros; Ren-Hua Fan; Matthew D Casselman; Gang Cheng; Hari R Khatri; Alexander Wei
Journal:  J Org Chem       Date:  2014-05-12       Impact factor: 4.354
  8 in total

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