Literature DB >> 28906121

N-Heterocyclic Carbene Catalyzed Stereoselective Glycosylation of 2-Nitrogalactals.

Jia-Lin Liu1, Yu-Tong Zhang1, Hang-Fan Liu1, Ling Zhou1, Jie Chen1.   

Abstract

An efficient N-heterocyclic carbene catalyzed glycosylation of 2-nitrogalactals with alcohols and phenol has been developed for the first time. A wide variety of 1,2-cis-2-nitroglycosides can be obtained with good to excellent yields and high to excellent α-selectivities.

Entities:  

Year:  2017        PMID： 28906121     DOI： 10.1021/acs.orglett.7b02543

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


  5 in total

Review 1.  Methods for 2-Deoxyglycoside Synthesis.

Authors:  Clay S Bennett; M Carmen Galan
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

Review 2.  Recent Advances in Stereoselective Chemical O-Glycosylation Reactions.

Authors:  Mana Mohan Mukherjee; Rina Ghosh; John A Hanover
Journal:  Front Mol Biosci       Date:  2022-06-14

3.  Stereoselective organocatalyzed glycosylations - thiouracil, thioureas and monothiophthalimide act as Brønsted acid catalysts at low loadings.

Authors:  G A Bradshaw; A C Colgan; N P Allen; I Pongener; M B Boland; Y Ortin; E M McGarrigle
Journal:  Chem Sci       Date:  2018-10-22       Impact factor: 9.825

4.  Matching Glycosyl Donor Reactivity to Sulfonate Leaving Group Ability Permits SN2 Glycosylations.

Authors:  Ming-Hua Zhuo; David J Wilbur; Eugene E Kwan; Clay S Bennett
Journal:  J Am Chem Soc       Date:  2019-10-09       Impact factor: 15.419

5.  Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides from Glycals Using B(C6F5)3 as Catalyst.

Authors:  Abhijit Sau; Carlos Palo-Nieto; M Carmen Galan
Journal:  J Org Chem       Date:  2019-02-15       Impact factor: 4.354
  5 in total

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