145362-72-7

Usage

Chemical Properties

White Solid

InChI:InChI=1/C23H21NO3/c25-16-21(23(26)27-17-18-10-4-1-5-11-18)24-22(19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-15,21,25H,16-17H2/t21-/m0/s1

Upstream product

• 100-51-6 benzyl alcohol 
• 1013-88-3 Benzophenone imine 
• 60022-62-0 L-serine benzyl ester hydrochloride 

Downstream Products

• 172325-03-0 N-diphenylmethylene-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester 
• 172325-20-1 N-diphenylmethylene-O-(3,4,6-tri-O-acetyl-2-deoxy-2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-β-D-glucopyranosyl)-L-serine benzyl ester 
• 172487-79-5 N-diphenylmethylene-O-4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl>-L-serine benzyl ester 
• 172325-05-2 N-diphenylmethylene-O-4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl>-L-serine benzyl ester 
• 337903-61-4 benzyl N-diphenylmethylene-O-(2,3,4,2',3',4',6'-hepta-O-acetyl-β-melibiosyl)-L-serinate 
• 337903-59-0 benzyl N-diphenylmethylene-O-(2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactosyl)-L-serinate 
• 188934-97-6 benzyl N-diphenylmethylene-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-serinate 
• 172487-73-9 N-diphenylmethylene-O-4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl>-L-serine benzyl ester 
• 172487-75-1 N-(9-fluorenylmethoxycarbonyl)-O-4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl>-L-serine benzyl ester 
• 172325-13-2 N-(9-fluorenylmethoxycarbonyl)-O-4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl>-L-serine benzyl ester 
• 172325-19-8 N-diphenylmethylene-O-4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-α-D-glucopyranosyl>-L-serine benzyl ester 
• 172487-78-4 N-diphenylmethylene-O-4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-α-D-mannopyranosyl>-L-serine benzyl ester 
• 172325-09-6 O-4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl>-L-serine benzyl ester 
• 172487-80-8 O-4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl>-L-serine benzyl ester 

Relevant academic research and scientific papers

Serine and threonine Schiff base esters react with β-anomeric peracetates in the presence of BF3·Et2O to produce β-glycosides

Improved procedures are reported for the glycosylation of L-serine and L-threonine utilizing activated Schiff base glycosyl acceptors, which are less expensive and more efficient alternatives to published methods. L-serine or L-threonine benzyl ester hydrochloride salts were reacted with the diarylketimine bis-(4-methoxyphenyl)-methanimine in CH3CN at rt to form the more nucleophilic Schiff bases 3a and 3b in excellent yield. These Schiff bases exhibited ring-chain tautomerism in CDCl3 as shown by 1H NMR. Schiff bases 3a and 3b, acting as glycosyl acceptors, reacted at rt with simple sugar peracetate donors with BF3·OEt 2 promotion to provide the corresponding L-serine and L-threonine O-linked glycosides in excellent yields and purities. The dipeptide ester Schiff base Ar2C = N-Ser-Val-OCH3 3e also reacted to provide β-glycosides in excellent yields, and without epimerization. With microwave irradiation the reactions were complete in 2 to 5 min. To investigate this reaction further, classical AgOTf-promoted Koenigs-Knorr reaction of D-glucopyranosyl, lactosyl, and maltosyl bromides were examined, providing the β-glycosides with yields ranging from 35% to 68%. The difference in reactivity between α- and β-carbohydrate peracetate donors was remarkable. The less configurationally stable D-xylopyranosyl tetra-acetate (a pentose) showed no selectivity (αvsβ-configuration) toward the Schiff bases. Copyright Taylor & Francis Group, LLC.

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.