Ontology highlight
ABSTRACT:
SUBMITTER: Park J
PROVIDER: S-EPMC2533432 | biostudies-literature | 2007 May
REPOSITORIES: biostudies-literature
Park Jin J Kawatkar Sameer S Kim Jin-Hwan JH Boons Geert-Jan GJ
Organic letters 20070414 10
TMSOTf-promoted glycosylations of 2-azido-2-deoxy-glucosyl trichloroacetimidates provide excellent alpha-anomeric selectivities when performed at a relatively high reaction temperature in the presence of PhSEt or thiophene. NMR and computation studies have shown that these glycosylations proceed through an equatorial anomeric sulfonium ion, which upon displacement by a sugar alcohol provides an axial glycoside. Computational studies have indicated that steric factors determine the selective form ...[more]