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The influence of various silyl protecting groups on 2-deoxyrhamnosylation using 2-deoxyrhamnosyl acetates, thioglycosides, and (p-methoxyphenyl)vinylbenzoate (PMPVB) donors has been presented. C-Glycosylation reactions reveal that tert-butyldimethylsilyl (TBDMS), triisopropylsilyl (TIPS), and tert-butyldiphenylsilyl (TBDPS) silyl protected rhamnosyl oxocarbenium ions have no facial selectivity except for the conformationally (4H3) locked tetraisopropyldisiloxane (TIPDS) protected rhamnose donor, which provides complete α-selectivity. However, TBDPS protected rhamnosyl donors are found to be superior protecting groups for α-stereoselective O-glycosylation reactions with various acceptors. The observed results are found consistent across donors and donor activation conditions. Most importantly, the study was conducted at room temperature unlike the other energy-intensive low-temperature studies and was bound to have more practical utility. The outcomes have been explained using kinetic and thermodynamic analyses.
Ananya Mukherji, and
Mahendra K V Rotta, and
Bikash K Sarmah, and
Pavan K Kancharla
April 2001,
Journal of the American Chemical Society,
Ananya Mukherji, and
Mahendra K V Rotta, and
Bikash K Sarmah, and
Pavan K Kancharla
September 2011,
Chemistry (Weinheim an der Bergstrasse, Germany),
Ananya Mukherji, and
Mahendra K V Rotta, and
Bikash K Sarmah, and
Pavan K Kancharla
June 2013,
Organic letters,
Ananya Mukherji, and
Mahendra K V Rotta, and
Bikash K Sarmah, and
Pavan K Kancharla
July 2012,
Angewandte Chemie (International ed. in English),
Ananya Mukherji, and
Mahendra K V Rotta, and
Bikash K Sarmah, and
Pavan K Kancharla
January 2005,
Nucleosides, nucleotides & nucleic acids,
Ananya Mukherji, and
Mahendra K V Rotta, and
Bikash K Sarmah, and
Pavan K Kancharla
January 1987,
Nucleic acids symposium series,
Ananya Mukherji, and
Mahendra K V Rotta, and
Bikash K Sarmah, and
Pavan K Kancharla
October 2010,
Molecules (Basel, Switzerland),
Ananya Mukherji, and
Mahendra K V Rotta, and
Bikash K Sarmah, and
Pavan K Kancharla
August 2003,
Organic letters,
Ananya Mukherji, and
Mahendra K V Rotta, and
Bikash K Sarmah, and
Pavan K Kancharla
October 2007,
The Journal of organic chemistry,
Ananya Mukherji, and
Mahendra K V Rotta, and
Bikash K Sarmah, and
Pavan K Kancharla
May 1957,
The Journal of pharmacology and experimental therapeutics,
