Open AccessReagent Controlled Direct Dehydrative Glycosylation with 2-Deoxy Sugars: Construction of the Saquayamycin Z Pentasaccharide
Author(s) -
J. Colin Mizia,
Clay S. Bennett
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b02056
Subject(s) - chemistry , glycosylation , reagent , anomer , glycosidic bond , yield (engineering) , total synthesis , selectivity , stereochemistry , sequence (biology) , combinatorial chemistry , organic chemistry , catalysis , biochemistry , enzyme , materials science , metallurgy
The first synthesis of the pentasaccharide fragment of the angucycline antibiotic saquayamycin Z is described. By using our sulfonyl chloride mediated reagent controlled dehydrative glycosylation, we are able to assemble the glycosidic linkages with high levels of anomeric selectivity. The total synthesis was completed in 25 total steps, and in 2.5% overall yield with a longest linear sequence of 15 steps.