Literature DB >> 21355584

Borinic acid-catalyzed regioselective acylation of carbohydrate derivatives.

Doris Lee1, Mark S Taylor.   

Abstract

Reversible covalent interactions of organoboron compounds are exploited as the basis for regioselective borinic acid-catalyzed acylations of polyols. This catalytic protocol enables differentiation of the secondary OH groups of a wide range of carbohydrate derivatives with diverse acid chloride and chloroformate reagents, using a structurally simple diarylborinic acid-derived catalyst.

Entities:  

Year:  2011        PMID： 21355584     DOI： 10.1021/ja110332r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  37 in total

1.  De novo asymmetric synthesis of the mezzettiaside family of natural products via the iterative use of a dual B-/Pd-catalyzed glycosylation.

Authors:  Sumit O Bajaj; Ehesan U Sharif; Novruz G Akhmedov; George A O'Doherty
Journal:  Chem Sci       Date:  2014-06       Impact factor: 9.825

Review 2.  Recent advances in site-selective functionalization of carbohydrates mediated by organocatalysts.

Authors:  Stephanie A Blaszczyk; Timothy C Homan; Weiping Tang
Journal:  Carbohydr Res       Date:  2018-11-23       Impact factor: 2.104

3.  Practical silyl protection of ribonucleosides.

Authors:  Thomas P Blaisdell; Sunggi Lee; Pinar Kasaplar; Xixi Sun; Kian L Tan
Journal:  Org Lett       Date:  2013-09-03       Impact factor: 6.005

Review 4.  Synthesis of carbohydrate building blocks via regioselective uniform protection/deprotection strategies.

Authors:  Tinghua Wang; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2019-05-02       Impact factor: 3.876

Review 5.  Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.

Authors:  Inji Shin; Michael J Krische
Journal:  Top Curr Chem       Date:  2016

6.  Synthesis and Structure-Activity Relationship Study of 5a-Carbasugar Analogues of SL0101.

Authors:  Mingzong Li; Yu Li; Roman M Mrozowski; Zachary M Sandusky; Mingde Shan; Xiwen Song; Bulan Wu; Qi Zhang; Deborah A Lannigan; George A O'Doherty
Journal:  ACS Med Chem Lett       Date:  2014-11-26       Impact factor: 4.345

7.  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

8.  A Comparison of the Structure and Bonding in the Aliphatic Boronic R-B(OH)2 and Borinic R-BH(OH) acids (R=H; NH2, OH, and F): A Computational Investigation.

Authors:  Niny Z Rao; Joseph D Larkin; Charles W Bock
Journal:  Struct Chem       Date:  2015-12-30       Impact factor: 1.887

9.  Diastereo- and Enantioselective Iridium Catalyzed Coupling of Vinyl Aziridines with Alcohols: Site-Selective Modification of Unprotected Diols and Synthesis of Substituted Piperidines.

Authors:  Gang Wang; Jana Franke; Chinh Q Ngo; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-06-15       Impact factor: 15.419

Review 10.  Synthesis of 5'-O-DMT-2'-O-TBS Mononucleosides Using an Organic Catalyst.

Authors:  Sunggi Lee; Thomas P Blaisdell; Pinar Kasaplar; Xixi Sun; Kian L Tan
Journal:  Curr Protoc Nucleic Acid Chem       Date:  2014-06-24
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