Literature DB >> 19780574

Brønsted acid-promoted glycosylations of disaccharide glycal substructures of the saccharomicins.

Bradley R Balthaser1, Frank E McDonald.   

Abstract

An acid-promoted glycosylation and alkynol cycloisomerization sequence provided direct access to the 2-deoxytrisaccharide corresponding to the fucose-saccharosamine-digitoxose substructure of saccharomicin B. In the course of this work, the absolute stereochemistry of the repeating fucose-saccharosamine disaccharide of saccharomicins was also confirmed.

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Year:  2009        PMID： 19780574      PMCID： PMC2783931          DOI： 10.1021/ol901923x

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


  11 in total

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Authors:  Joseph M Pletcher; Frank E McDonald
Journal:  Org Lett       Date:  2005-10-13       Impact factor: 6.005

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6.  Stereoselective synthesis of vancosamine and saccharosamine glycals via tungsten-catalyzed alkynol cycloisomerization.

Authors:  William W Cutchins; Frank E McDonald
Journal:  Org Lett       Date:  2002-03-07       Impact factor: 6.005

7.  Generation of reactive species by one-electron reduction of Fischer-type carbene complexes of group 6 metals and their use for carbon-carbon bond formation.

Authors:  Kohei Fuchibe; Nobuharu Iwasawa
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8.  Stereoselective synthesis of L-oliose trisaccharide via iterative alkynol cycloisomerization and acid-catalyzed glycosylation.

Authors:  Frank E McDonald; Minglang Wu
Journal:  Org Lett       Date:  2002-10-31       Impact factor: 6.005

9.  [W(CO)5]-catalyzed endo- or exo-cycloisomerization reactions of 1,1-disubstituted 4-pentyn-1-ols: experimental and theoretical studies.

Authors:  José Barluenga; Alejandro Diéguez; Félix Rodríguez; Francisco J Fañanás; Tomás Sordo; Pablo Campomanes
Journal:  Chemistry       Date:  2005-09-19       Impact factor: 5.236

10.  Stereoselective synthesis of d-desosamine and related glycals via tungsten-catalyzed alkynol cycloisomerization.

Authors:  Mary H Davidson; Frank E McDonald
Journal:  Org Lett       Date:  2004-05-13       Impact factor: 6.005
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  7 in total

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Journal:  Org Lett       Date:  2018-11-14       Impact factor: 6.005

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Journal:  J Am Chem Soc       Date:  2021-02-08       Impact factor: 15.419

5.  Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide.

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Journal:  Org Lett       Date:  2020-04-13       Impact factor: 6.005

6.  Stereospecific Synthesis of the Saccharosamine-Rhamnose-Fucose Fragment Present in Saccharomicin B.

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Journal:  Org Lett       Date:  2018-07-17       Impact factor: 6.005

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  7 in total

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