Solid-Phase Synthesis of Di-N-Acetyl-β-Chitobiosyl NAG-Thiazoline

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.

Cite this article as:

Huang Gangliang and Chen Ya, Solid-Phase Synthesis of Di-N-Acetyl-β-Chitobiosyl NAG-Thiazoline, Letters in Drug Design & Discovery 2011; 8 (7) . https://dx.doi.org/10.2174/157018011796235220