145362-72-7

Basic information

• Product Name: BENZYL N-(DIPHENYLMETHYLENE)-L-SERINATE
• Synonyms: BENZYL N-(DIPHENYLMETHYLENE)-L-SERINATE;N-(DIPHENYLMETHYLENE)-L-SERINE BENZYL ESTER;N-(DiphenylMethylene)-L-serine PhenylMethyl Ester
• CAS NO: 145362-72-7
• Molecular Formula: C₂₃H₂₁NO₃
• Molecular Weight: 359.42
• Product Categories: Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Aromatics
• Mol File: 145362-72-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 78-80 °C
• Boiling Point: 514.6°C at 760 mmHg
• Flash Point: 265°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 2.05E-11mmHg at 25°C
• Refractive Index: 1.577
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, Dichloromethane
• PKA: 13.96±0.10(Predicted)
• CAS DataBase Reference: BENZYL N-(DIPHENYLMETHYLENE)-L-SERINATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL N-(DIPHENYLMETHYLENE)-L-SERINATE(145362-72-7)
• EPA Substance Registry System: BENZYL N-(DIPHENYLMETHYLENE)-L-SERINATE(145362-72-7)

Safety Data

• Hazardous Substances Data: 145362-72-7(Hazardous Substances Data)

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

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

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 
• 172487-73-9 N-diphenylmethylene-O-4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl>-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 
• 337903-54-5 benzyl N-diphenylmethylene-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-L-serinate 
• 337903-56-7 benzyl N-diphenylmethylene-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-serinate 
• 188934-97-6 benzyl N-diphenylmethylene-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-serinate 
• 337903-45-4 benzyl N-diphenylmethylene-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-L-serinate 
• 337903-57-8 benzyl N-diphenylmethylene-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-serinate 

Relevant articles and documents

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.

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.