β-Selective mannosylation with a 4,6-silylene-tethered thiomannosyl donor
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β-Selective mannosylation with a 4,6-silylene-tethered thiomannosyl donor. / Heuckendorff, Mads; Bendix, Jesper; Pedersen, Christian Marcus; Bols, Mikael.
I: Organic Letters, Bind 16, Nr. 4, 2014, s. 1116-9.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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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
Y1 - 2014
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
VL - 16
SP - 1116
EP - 1119
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 4
ER -
ID: 109743278