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

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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.
OriginalsprogEngelsk
TidsskriftOrganic Letters
Vol/bind16
Udgave nummer4
Sider (fra-til)1116-9
Antal sider4
ISSN1523-7060
DOI
StatusUdgivet - 2014

ID: 109743278