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

Pablo Tovillas | Zendy; Iván Lavandera García | Zendy; Paula Oroz | Zendy; Nuria Mazo | Zendy; Alberto Avenoza | Zendy; Francisco Corzana | Zendy; Gonzalo JiménezOsés | Zendy; Jesús H. Busto | Zendy; Jesús M. Peregrina | Zendy

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

Author(s) -

Pablo Tovillas,

Iván Lavandera García,

Paula Oroz,

Nuria Mazo,

Alberto Avenoza,

Francisco Corzana,

Gonzalo JiménezOsés,

Jesús H. Busto,

Jesús M. Peregrina

Publication year - 2018

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.7b03225

Subject(s) - chemistry , nucleophile , carbohydrate , ring (chemistry) , stereochemistry , organic chemistry , catalysis

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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