Literature DB >> 20961035

Adaptable synthesis of C-glycosidic multivalent carbohydrates and succinamide-linked derivatization.

Gavin J Miller1, John M Gardiner.   

Abstract

A modular approach to the synthesis of trivalent C-glycosidic carbohydrates is described. The approach is illustrated employing carboxylate-terminated C-glycosidic d-mannose, d-glucose, and d-galactose derivatives with different length C1-linked spacer units and also core units with different length linker units attached. The central core scaffold is additionally functionalized via a succinamide-based, conjugatable linker unit, exemplified in an extended multivalent derivative [31] and a pyrene-bearing fluorsecent-labeled tris-C-mannosyl conjugate [33].

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Year:  2010        PMID: 20961035     DOI: 10.1021/ol102310x

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


  4 in total

1.  Cation Clock Reactions for the Determination of Relative Reaction Kinetics in Glycosylation Reactions: Applications to Gluco- and Mannopyranosyl Sulfoxide and Trichloroacetimidate Type Donors.

Authors:  Philip O Adero; Takayuki Furukawa; Min Huang; Debaraj Mukherjee; Pascal Retailleau; Luis Bohé; David Crich
Journal:  J Am Chem Soc       Date:  2015-08-07       Impact factor: 15.419

2.  Using NMR to Dissect the Chemical Space and O-Sulfation Effects within the O- and S-Glycoside Analogues of Heparan Sulfate.

Authors:  Maria C Z Meneghetti; Lucy Naughton; Conor O'Shea; Dindet S-E Koffi Teki; Vincent Chagnault; Helena B Nader; Timothy R Rudd; Edwin A Yates; José Kovensky; Gavin J Miller; Marcelo A Lima
Journal:  ACS Omega       Date:  2022-07-08

3.  Synthesis of β-C-galactosyl D- and L-alanines.

Authors:  V Narasimharao Thota; Jacquelyn Gervay-Hague; Suvarn S Kulkarni
Journal:  Org Biomol Chem       Date:  2012-10-28       Impact factor: 3.876

4.  Mild Cu(OTf)2-Mediated C-Glycosylation with Chelation-Assisted Picolinate as a Leaving Group.

Authors:  Wenjing Ye; Christopher M Stevens; Peng Wen; Christopher J Simmons; Weiping Tang
Journal:  J Org Chem       Date:  2020-08-05       Impact factor: 4.354

  4 in total

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