Literature DB >> 19924835

Highly stereoselective synthesis of alpha-D-mannopyranosyl phosphosugars.

David Crich1, Sébastien Picard.   

Abstract

Alpha-mannopyranosyl phosphosugars are obtained in 61-90% yields from 4,6-O-benzylidene-protected mannosyl thioglycosides bearing ester functionality in the 3-O-position by coupling reactions with ammonium salts of phosphosugars on activation with 1-benzenesulfinyl piperidine, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride. Due to the presence of the disarming ester group, only the formation of the alpha-isomer was observed.

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Year:  2009        PMID： 19924835      PMCID： PMC2852025          DOI： 10.1021/jo902254w

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


  18 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.  Efficient, diastereoselective chemical synthesis of a beta-mannopyranosyl phosphoisoprenoid.

Authors:  D Crich; V Dudkin
Journal:  Org Lett       Date:  2000-11-30       Impact factor: 6.005

Review 3.  Lysosomal enzymes and their receptors.

Authors:  K von Figura; A Hasilik
Journal:  Annu Rev Biochem       Date:  1986       Impact factor: 23.643

4.  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

5.  1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages.

Authors:  D Crich; M Smith
Journal:  J Am Chem Soc       Date:  2001-09-19       Impact factor: 15.419

6.  New principles for glycoside-bond formation.

Authors:  Xiangming Zhu; Richard R Schmidt
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

7.  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

8.  Does neighboring group participation by non-vicinal esters play a role in glycosylation reactions? Effective probes for the detection of bridging intermediates.

Authors:  David Crich; Tianshun Hu; Feng Cai
Journal:  J Org Chem       Date:  2008-10-22       Impact factor: 4.354

9.  Block synthesis of tetra- and hexasaccharides (beta-D-glycero-D-manno-Hep p-(1-->4)-[alpha-l-Rha p-(1-->3)-beta-D-glycero-D-manno-Hep p-(1-->4)]n-alpha-L-Rha p-OMe (n = 1 and 2)) corresponding to multiple repeat units of the glycan from the surface-layer glycoprotein from Bacillus thermoaerophilus.

Authors:  David Crich; Ming Li
Journal:  J Org Chem       Date:  2008-08-27       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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  5 in total

1.  Influence of the O3 protecting group on stereoselectivity in the preparation of C-mannopyranosides with 4,6-O-benzylidene protected donors.

Authors:  David Crich; Indrajeet Sharma
Journal:  J Org Chem       Date:  2010-11-11       Impact factor: 4.354

2.  Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A via convergent B(C6F5)3-catalyzed glycosylation of sterically-hindered precursors.

Authors:  Rashad R Karimov; Derek S Tan; David Y Gin
Journal:  Chem Commun (Camb)       Date:  2017-05-30       Impact factor: 6.222

3.  Bioresponsive deciduous-charge amphiphiles for liposomal delivery of DNA and siRNA.

Authors:  Philippe Pierrat; Dimitri Kereselidze; Patrick Wehrung; Guy Zuber; Françoise Pons; Luc Lebeau
Journal:  Pharm Res       Date:  2013-02-01       Impact factor: 4.200

4.  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

5.  Stereoselective gold(I)-catalyzed approach to the synthesis of complex α-glycosyl phosphosaccharides.

Authors:  Xiaojuan Zhang; Yutong Yang; Jiahao Ding; Yun Zhao; Hongbin Zhang; Yugen Zhu
Journal:  Nat Commun       Date:  2022-01-20       Impact factor: 17.694
  5 in total

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