Formation of β-Configured Thioglycosides of D-Glucosamine and D-Galactosamine and Synthesis of Protected Human Milk Oligosaccharides

TY - JOUR

T1 - Formation of β-Configured Thioglycosides of D-Glucosamine and D-Galactosamine and Synthesis of Protected Human Milk Oligosaccharides

AU - Pedersen, Kamilla

AU - Christensen, Louise G.

AU - Jensen, Henrik H.

N1 - Publisher Copyright: © 2023 American Chemical Society.

PY - 2023/9/1

Y1 - 2023/9/1

N2 - We report on the stereoselective multigram scale preparation of cyclohexyl- and phenyl thioglycosides of 2-azido-2-deoxy-β-d-gluco- and galactopyranosides from d-N-acetylglucosamine using a catalytic and solvent-free method. Two of the prepared building blocks were used as key intermediates for the synthesis of human milk oligosaccharides LNT and LNnT in their protected form.

AB - We report on the stereoselective multigram scale preparation of cyclohexyl- and phenyl thioglycosides of 2-azido-2-deoxy-β-d-gluco- and galactopyranosides from d-N-acetylglucosamine using a catalytic and solvent-free method. Two of the prepared building blocks were used as key intermediates for the synthesis of human milk oligosaccharides LNT and LNnT in their protected form.

UR - http://www.scopus.com/inward/record.url?scp=85169162127&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.3c01267

DO - 10.1021/acs.joc.3c01267

M3 - Journal article

C2 - 37560896

AN - SCOPUS:85169162127

SN - 0022-3263

VL - 88

SP - 12531

EP - 12541

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -