Literature DB >> 12027647

Efficient synthesis of the hexasaccharide fragment of landomycin A: using phenyl 2,3-O-thionocarbonyl-1-thioglycosides as 2-deoxy-beta-glycoside precursors.

Biao Yu1, Ping Wang.   

Abstract

[carbohydrate structure: see text] The beta-p-methoxyphenol hexadeoxysaccharide fragment of landomycin A was synthesized in a total of 33 steps and 0.5% overall yield starting from D-mannose and D-xylose, featuring the use of phenyl 2,3-O-thionocarbonyl-1-thioglycosides as 2-deoxy-beta-glycoside precursors.

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Year:  2002        PMID: 12027647     DOI: 10.1021/ol0259286

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


  9 in total

1.  Recent Advances in Transition Metal-Catalyzed Glycosylation.

Authors:  Matthew J McKay; Hien M Nguyen
Journal:  ACS Catal       Date:  2012-06-14       Impact factor: 13.084

2.  Synthesis of the Hexasaccharide Fragment of Landomycin A Using a Mild, Reagent-Controlled Approach.

Authors:  Subbarao Yalamanchili; Dina Lloyd; Clay S Bennett
Journal:  Org Lett       Date:  2019-04-25       Impact factor: 6.005

Review 3.  Delineation of gilvocarcin, jadomycin, and landomycin pathways through combinatorial biosynthetic enzymology.

Authors:  Madan K Kharel; Jürgen Rohr
Journal:  Curr Opin Chem Biol       Date:  2012-03-30       Impact factor: 8.822

4.  Reagent Controlled Direct Dehydrative Glycosylation with 2-Deoxy Sugars: Construction of the Saquayamycin Z Pentasaccharide.

Authors:  J Colin Mizia; Clay S Bennett
Journal:  Org Lett       Date:  2019-07-15       Impact factor: 6.005

5.  Automated, Multistep Continuous-Flow Synthesis of 2,6-Dideoxy and 3-Amino-2,3,6-trideoxy Monosaccharide Building Blocks.

Authors:  Subbarao Yalamanchili; Tu-Anh Nguyen; Alexander Zsikla; Gavin Stamper; Ashley E DeYong; John Florek; Olivea Vasquez; Nicola L B Pohl; Clay S Bennett
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-21       Impact factor: 16.823

6.  Phenyl 2,3-O-isopropyl-idene-1-thio-α-d-rhamnopyran-oside.

Authors:  Hasnah Osman; David S Larsen; Lyall R Hanton; Jim Simpson
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2007-12-06

7.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors:  Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419

8.  Scope and limitations of 2-deoxy- and 2,6-dideoxyglycosyl bromides as donors for the synthesis of β-2-deoxy- and β-2,6-dideoxyglycosides.

Authors:  Miho Kaneko; Seth B Herzon
Journal:  Org Lett       Date:  2014-05-01       Impact factor: 6.005

9.  Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties.

Authors:  Yao-Hsuan Lai; Soumik Mondal; Hsin-Tzu Su; Sheng-Cih Huang; Mine-Hsine Wu; I-Wen Huang; Tsai-Ling Yang Lauderdale; Jen-Shin Song; Kak-Shan Shia; Kwok-Kong Tony Mong
Journal:  RSC Adv       Date:  2021-03-02       Impact factor: 3.361

  9 in total

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