219693-08-0

Upstream product

• 172490-46-9 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 337903-44-3 2,2,2-trichloroethyloxycarbonyl-amino perbenzoylglucosamine 

Downstream Products

• 219693-10-4 2-acetamido-1,6-di-O-acetyl-3-O-benzoyl-2-deoxy-4-thio-4-S-[3,4,6-tri-O-benzoyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-α-D-glucopyranose 
• 337903-64-7 benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-benzoyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate 
• 337903-75-0 benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-benzoyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-serinate 

Relevant academic research and scientific papers

Facile and efficient access to C1-aminosugar derivatives under mild conditions

A facile and efficient synthesis of C1-aminosugar derivatives under catalyst-free conditions is described here. In particular, readily available benzoyl glycosyl bromides react smoothly to give a broad scope of C1-aminosugar derivatives in good yields. Th

Solid-phase synthesis of O-linked glycopeptide analogues of enkephalin

The synthesis of 18 N-α-FMOC-amino acid glycosides for solid-phase glycopeptide assembly is reported. The glycosides were synthesized either from the corresponding O'Donnell Schiff bases or from N-α-FMOC-amino protected serine or threonine and the appropriate glycosyl bromide using Hanessian's modification of the Koenigs-Knorr reaction. Reaction rates of D-glycosyl bromides (e.g., acetobromoglucose) with the L- and D-forms of serine and threonine are distinctly different and can be rationalized in terms of the steric interactions within the two types of diastereomeric transition states for the D/L and D/D reactant pairs. The N-α-FMOC-protected glycosides [monosaccharides Xyl, Glc, Gal, Man, GlcNAc, and GalNAc; disaccharides Gal-β(1-4)-Glc (lactose), Glc-β(1-4)-Glc (cellobiose), and Gal-α(1-6)-Glc (melibiose)] were incorporated into 22 enkephalin glycopeptide analogues. These peptide opiates bearing the pharmacophore H-Tyr-c[DCys-Gly-Phe-DCys]- were designed to probe the significance of the glycoside moiety and the carbohydrate-peptide linkage region in blood-brain barrier (BBB) transport, opiate receptor binding, and analgesia.

Synthesis of S-linked thiooligosaccharide analogues of Nod factors. Part 1: Selectively N-protected 4-thiochitobiose precursors

The synthesis of S-linked thio-analogues of chitobiose diversely substituted at both 2-acetamido-2-deoxy-D-glucopyranosyl units has been achieved successfully starting either from a 1,6-anhydro-4-O-triflyl galactosaminide derivative in reaction with a glucosamide 1-thiolate in DMF or a 1,6-anhydro-4-thiolate of a D-glucosaminide derivative with a Troc-protected 2-amino-2-deoxy-D-glucose derivative. Alternatively, reaction of an acylated 4-thiolate of 2-acetamido-2-deoxy glucose with an N-Troc-protected glucosaminyl bromide afforded the expected S-linked 4-thio-analogue of chitobiose. Acid catalysis involving reaction of compound 17 with an N-Troc-protected glucosaminyl imidate in the presence of trimethylsilyl triflate gave only poor yields of the expected 1,6-anhydro 4-thio-S-linked disaccharide.