Literature DB >> 23239901

MILD AND SELECTIVE O-GLYCOSYLATIONS OF PRIMARY ALCOHOLS WITH THE THIOGLUCOSAMINIDE DERIVATIVE PROMOTED BY N-IODOSUCCINIMIDE AND HBF(4)-ADOSROBED ON SILICA GEL.

Michio Kurosu1, Kai Li.   

Abstract

Selective glycosylations of primary alcohols with the thioglucosaminide 1 are achieved by using NIS and HBF(4)-SiO(2). HBF(4)-SiO(2) is a mild Brønsted acid which requires primary alcohols or phenols to effectively activate 1 with NIS at rt. A wide range of functional groups are tolerated under these conditions.

Entities:  

Year:  2009        PMID： 23239901      PMCID： PMC3518929          DOI： 10.3987/com-09-s(s)24

Source DB:  PubMed          Journal:  Heterocycles        ISSN： 0385-5414            Impact factor:   0.831


  12 in total

Review 1.  Formulation strategies for absorption windows.

Authors:  Stanley S Davis
Journal:  Drug Discov Today       Date:  2005-02-15       Impact factor: 7.851

Review 2.  Prodrug strategies in anticancer chemotherapy.

Authors:  Felix Kratz; Ivonne A Müller; Claudia Ryppa; André Warnecke
Journal:  ChemMedChem       Date:  2008-01       Impact factor: 3.466

3.  Development of a cy3-labeled glucose bioprobe and its application in bioimaging and screening for anticancer agents.

Authors:  Jongmin Park; Hyang Yeon Lee; Myung-Haing Cho; Seung Bum Park
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Potent renin inhibitory peptides containing hydrophilic end groups.

Authors:  G L Bundy; D T Pals; J A Lawson; S J Couch; M F Lipton; M A Mauragis
Journal:  J Med Chem       Date:  1990-08       Impact factor: 7.446

5.  Glycosylated flavones as selective inhibitors of topoisomerase IV.

Authors:  F X Bernard; S Sablé; B Cameron; J Provost; J F Desnottes; J Crouzet; F Blanche
Journal:  Antimicrob Agents Chemother       Date:  1997-05       Impact factor: 5.191

6.  Glycosylation improves the central effects of DAMGO.

Authors:  John J Lowery; Larisa Yeomans; Charles M Keyari; Peg Davis; Frank Porreca; Brian I Knapp; Jean M Bidlack; Edward J Bilsky; Robin Polt
Journal:  Chem Biol Drug Des       Date:  2007-01       Impact factor: 2.817

7.  Highly efficient O-glycosylations with p-tolyl thioribosides and p-TolSOTf.

Authors:  Michio Kurosu; Kai Li
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

8.  [Synthesis of partial structure of complex types of N-glycoproteins].

Authors:  H Paulsen; B Helpap
Journal:  Carbohydr Res       Date:  1991-09-02       Impact factor: 2.104

9.  Enhanced efficacy of 7-hydroxy-3-methoxycadalene via glycosylation in in vivo xenograft study.

Authors:  Hyang Yeon Lee; Jung-Taek Kwon; Minseob Koh; Myung-Haing Cho; Seung Bum Park
Journal:  Bioorg Med Chem Lett       Date:  2007-09-01       Impact factor: 2.823

10.  Hydrolytic reactivity trends among potential prodrugs of the O2-glycosylated diazeniumdiolate family. Targeting nitric oxide to macrophages for antileishmanial activity.

Authors:  Carlos A Valdez; Joseph E Saavedra; Brett M Showalter; Keith M Davies; Thomas C Wilde; Michael L Citro; Joseph J Barchi; Jeffrey R Deschamps; Damon Parrish; Stefan El-Gayar; Ulrike Schleicher; Christian Bogdan; Larry K Keefer
Journal:  J Med Chem       Date:  2008-06-06       Impact factor: 7.446
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  1 in total

1.  Chemical synthesis of 4-azido-β-galactosamine derivatives for inhibitors of N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase.

Authors:  Seanghai Hor; Takumi Kodama; Nobuo Sugiura; Hikaru Kondou; Mio Yanagida; Keiya Yanagisawa; Aoki Shibasawa; Bunta Tsuzuki; Naoto Fukatsu; Kazuya Nagao; Kenji Yamana; Kazuya I P J Hidari; Hideto Watanabe; Osami Habuchi; Hirofumi Nakano
Journal:  Glycoconj J       Date:  2018-09-01       Impact factor: 2.916
  1 in total

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