Neighboring Group Participation in Glycosylation Reactions by 2,6-Disubstituted 2-O-Benzoyl groups: A Mechanistic Investigation
作者： Rohan J. Williams , Nathan W. McGill , Jonathan M. White , Spencer J. Williams
DOI: 10.1080/07328303.2010.508141
关键词:
摘要: Variable yields and glycosylation stereoselectivity were obtained for NIS/TfOH-medi- ated reaction of 4-methoxyphenyl 2,4,6-tetra-O-acetyl-β-D-galactopyranoside thiogalactosides bearing acetyl, benzoyl, 2,6-dimethoxylbenzoyl, 2,4,6-trimethylbenzoyl, or 2,6-dichlorobenzoyl groups at the 2-positions acetyl remainder. X-ray structures 4-methylphenyl 2,3,4,6-tetra-O-(2,4,6-trimethylbenzoyl)-1-thio-β-D-galactopyr anoside 3,4-O-isopropylidene-2,6-di-O-(2,4,6-trimethylbenzoyl)-1-thio-β-D-galactopyranoside revealed slightly distorted 4 C 1 chair conformations. temperature NMR that activation 2,3,4,6-tetra-O-(2,4,6-trimethylbenzoyl)-1-thio-β-D-galactopyranoside afforded only dioxolenium ion, whereas 3,4,6-tri-O-acetyl-2-O-(2,4,6-trimethylbenzoyl)-1-thio-β-D-galactopyranoside gave a 1:1 mixture ion glycosyl triflate. However, intermediates formed from these deactivated donors do not influence ...
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