Nucleofuge Generating
Glycosidations by the Remote
Activation of Hydroxybenzotriazolyl Glycosides
Version 3 2017-10-20, 01:13
Version 2 2017-10-19, 11:33
Version 1 2017-10-18, 21:29
Posted on 2017-10-20 - 01:13
Hydroxybenzotriazole
is routinely used in peptide chemistry for
reducing racemization due to the increased reactivity. In this article,
very stable hydroxybenzotriazolyl glucosides were identified to undergo
glycosidation. The reaction was hypothesized to go through the remote
activation by the Tf2O at the N3-site of HOBt followed
by the extrusion of the oxocarbenium ion that was attacked by the
glycosyl acceptor. Further, equilibration of the zwitterionic benzotriazolyl
species makes the leaving group noncompetitive and generates the nucleofuge
that has been reconverted to the glycosyl donor. The reaction is mild,
high yielding, fast and suitable for donors containing both C2-ethers
and C2-esters as well. The regenerative-donor glycosidation strategy
is promising as it enables us to regenerate the glycosyl donor for
further utilization. The utility of the methodology for the oligosaccharide
synthesis was demonstrated by the successful synthesis of the branched
pentamannan core of the HIV1−gp120 complex.
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Neralkar, Mahesh; Mishra, Bijoyananda; Hotha, Srinivas (2017). Nucleofuge Generating
Glycosidations by the Remote
Activation of Hydroxybenzotriazolyl Glycosides. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.7b02027
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AUTHORS (3)
MN
Mahesh Neralkar
BM
Bijoyananda Mishra
SH
Srinivas Hotha