337903-59-0

Basic information

• Product Name: N-Diphenylmethylene-O-(2,3,6,2',3',4',6'-hepta-O-acetyl--D-lactosyl)-L-serine, Benzyl Ester
• Synonyms: N-Diphenylmethylene-O-(2,3,6,2',3',4',6'-hepta-O-acetyl--D-lactosyl)-L-serine, Benzyl Ester;N-(DiphenylMethylene)-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl]-L-serine PhenylMethyl Ester
• CAS NO: 337903-59-0
• Molecular Formula: C₄₉H₅₅NO₂₀
• Molecular Weight: 977.9557
• Product Categories: Oligosaccharides
• Mol File: 337903-59-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 901.5±65.0 °C(Predicted)
• Appearance: /
• Density: 1.33±0.1 g/cm3(Predicted)
• Solubility: Chloroform, Dichloromethane
• PKA: 1.98±0.50(Predicted)
• CAS DataBase Reference: N-Diphenylmethylene-O-(2,3,6,2',3',4',6'-hepta-O-acetyl--D-lactosyl)-L-serine, Benzyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Diphenylmethylene-O-(2,3,6,2',3',4',6'-hepta-O-acetyl--D-lactosyl)-L-serine, Benzyl Ester(337903-59-0)
• EPA Substance Registry System: N-Diphenylmethylene-O-(2,3,6,2',3',4',6'-hepta-O-acetyl--D-lactosyl)-L-serine, Benzyl Ester(337903-59-0)

Safety Data

• Hazardous Substances Data: 337903-59-0(Hazardous Substances Data)

Usage

Chemical Properties

White Foam

Uses

N-Diphenylmethylene-O-(2,3,6,2'',3'',4'',6''-hepta-O-acetyl-β-D-lactosyl)-L-serine, Benzyl Ester (cas# 337903-59-0) is a compound useful in organic synthesis.

Upstream product

• 1013-88-3 Benzophenone imine 
• 100-51-6 benzyl alcohol 
• 145362-72-7 N-diphenylmethylene-L-serine benzyl ester 
• 3616-19-1 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 
• 3616-19-1 lactose octaacetate 
• 60022-62-0 L-serine benzyl ester hydrochloride 

Downstream Products

• 169275-84-7 N^α-(9-fluorenylmethoxycarbonyl)-3-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O- acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl]-L-serine 

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.