β-Selective mannosylation with a 4,6-silylene-tethered thiomannosyl donor

TY - JOUR

T1 - β-Selective mannosylation with a 4,6-silylene-tethered thiomannosyl donor

AU - Heuckendorff, Mads

AU - Bendix, Jesper

AU - Pedersen, Christian Marcus

AU - Bols, Mikael

PY - 2014/2/21

Y1 - 2014/2/21

N2 - Mannosylations using the new conformationally restricted donor phenyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-1-thio-α-D-mannopyranoside (6) have been found to be β-selective with a variety of activation conditions. The simplest activation conditions were NIS/TfOH, in which case it is proposed that the β-mannoside is formed from β-selective glycosylation of the oxocarbenium ion 25 in a B(2,5) conformation.

AB - Mannosylations using the new conformationally restricted donor phenyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-1-thio-α-D-mannopyranoside (6) have been found to be β-selective with a variety of activation conditions. The simplest activation conditions were NIS/TfOH, in which case it is proposed that the β-mannoside is formed from β-selective glycosylation of the oxocarbenium ion 25 in a B(2,5) conformation.

U2 - 10.1021/ol403722f

DO - 10.1021/ol403722f

M3 - Journal article

C2 - 24502365

SN - 1523-7060

VL - 16

SP - 1116

EP - 1119

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -