145362-73-8

Upstream product

• 1013-88-3 Benzophenone imine 
• 5042-87-5 (2S,3R)-2-Amino-3-hydroxy-butyric acid benzhydryl ester; compound with toluene-4-sulfonic acid 
• 908093-98-1 diazodiphenylmethane 

Downstream Products

• 115054-57-4 O-diphenylmethyl-L-threonine 
• 172325-06-3 N-diphenylmethylene-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine diphenylmethyl ester 
• 172325-14-3 N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine diphenylmethyl ester 
• 172325-10-9 O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine diphenylmethyl ester 

Relevant academic research and scientific papers

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.

Method for making amino acid glycosides and glycopeptides

A compound of the formula STR1 is disclosed. X is selected from the group consisting of aryl, alkyl, imidate ester, imino ester, amidine, azide, isocyanate, and dithiocarbonate. R' is a group selected from the group consisting of groups containing a hydroxyl moiety, groups containing a protected hydroxyl moiety, and groups containing an O-linked sugar. G is a carbon chain of 0-10 carbons and R is not a methyl group and is a group capable of removal under conditions compatible with glycopeptide synthesis. In a preferred form the compound, R is selected from the group consisting of benzylic or allyl groups and X is CPh2. A method of forming a glycocide from the compound is also disclosed.