Title: Solid-Phase Synthesis of Di-N-Acetyl-β-Chitobiosyl NAG-Thiazoline
Volume: 8
Issue: 7
Author(s): Gangliang Huang and Ya Chen
Affiliation:
Keywords:
Di-N-acetyl-β-chitobiosyl NAG-thiazoline, Allosamidin analogue, Solid-phase synthesis, Trichloroacetimidate donors, Wang resin, Glycosylation reactions, chitinase, pseudodisaccharide, Streptomyces, thiazoline triacetate 6, Acetylation, TBDMS group, Wang-chlorinated resin, trichloroacetimidate, TMSOTf-promoted glycosylation
Abstract: The solid-phase synthesis of di-N-acetyl-β-chitobiosyl NAG (N-acetyl D-glucosamine)-thiazoline 3 was reported. After the 6-O-benzyl NAG-thiazoline 9, NHCbz trichloroacetimidate donors 14, and 21 were synthesized, and solid-phase synthesis was performed using the Wang resin as support. The target di-N-acetyl-β-chitobiosyl NAGthiazoline 3 was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively.
