Literature DB >> 17107090

Highly Diastereoselective thioglycosylation of functionalized peracetylated glycosides catalyzed by MoO2Cl2.

Shiue-Shien Weng1, Yow-Dzer Lin, Chien-Tien Chen.   

Abstract

Among 18 oxometallic species, MoO2Cl2 was found to be the most reactive in catalytic thioglycosylation of O-acetylated glycosides with functionalized thiols in CH2Cl2, leading cleanly to 1,2-trans-thioglycosides with exclusive diastereocontrol. The new catalytic protocol is applicable to a monoglycoside building block and beta-(1-->6)-S-linked-thiodisaccharide synthesis. [reaction: see text].

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Year:  2006        PMID: 17107090     DOI: 10.1021/ol062375g

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


  6 in total

1.  Thio-arylglycosides with various aglycon para-substituents: a probe for studying chemical glycosylation reactions.

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Journal:  Org Biomol Chem       Date:  2008-10-20       Impact factor: 3.876

2.  Synthesis and biological evaluation of a novel MUC1 glycopeptide conjugate vaccine candidate comprising a 4'-deoxy-4'-fluoro-Thomsen-Friedenreich epitope.

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Journal:  Beilstein J Org Chem       Date:  2015-01-23       Impact factor: 2.883

3.  Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions.

Authors:  Miqueas G Traverssi; Alicia B Peñéñory; Oscar Varela; Juan P Colomer
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Review 4.  One-pot construction of carbohydrate scaffolds mediated by metal catalysts.

Authors:  Mana Mohan Mukherjee; Sajal Kumar Maity; Rina Ghosh
Journal:  RSC Adv       Date:  2020-09-02       Impact factor: 4.036

5.  Straightforward Synthesis of the Poly(ADP-ribose) Branched Core Structure.

Authors:  Rui Hagino; Keita Mozaki; Naoko Komura; Akihiro Imamura; Hideharu Ishida; Hiromune Ando; Hide-Nori Tanaka
Journal:  ACS Omega       Date:  2022-09-05

6.  Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols.

Authors:  Tamashree Ghosh; Abhishek Santra; Anup Kumar Misra
Journal:  Beilstein J Org Chem       Date:  2013-05-22       Impact factor: 2.883

  6 in total

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