Literature DB >> 29638123

Tn Antigen Mimics by Ring-Opening of Chiral Cyclic Sulfamidates with Carbohydrate C1- S- and C1- O-Nucleophiles.

Pablo Tovillas1, Iván García1, Paula Oroz1, Nuria Mazo1, Alberto Avenoza1, Francisco Corzana1, Gonzalo Jiménez-Osés1, Jesús H Busto1, Jesús M Peregrina1.   

Abstract

Starting from commercially available ( S)-isoserine and effectively accessible ( S)-α-methylserine, enantiopure cyclic sulfamidates have been prepared as chiral building blocks for the synthesis of various S- and O-glycosylated amino acid derivatives, including unnatural variants of the Tn antigen, through highly chemo-, regio-, and stereoselective nucleophilic ring-opening reactions with carbohydrate C1- S- and C1- O-nucleophiles.

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Year:  2018        PMID: 29638123     DOI: 10.1021/acs.joc.7b03225

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  1 in total

1.  Synthesis of β2,2-Amino Acids by Stereoselective Alkylation of Isoserine Derivatives Followed by Nucleophilic Ring Opening of Quaternary Sulfamidates.

Authors:  Pablo Tovillas; Claudio D Navo; Paula Oroz; Alberto Avenoza; Francisco Corzana; María M Zurbano; Gonzalo Jiménez-Osés; Jesús H Busto; Jesús M Peregrina
Journal:  J Org Chem       Date:  2022-06-22       Impact factor: 4.198

  1 in total

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