337903-59-0

Usage

Uses

1. Used in Organic Synthesis:
N-Diphenylmethylene-O-(2,3,6,2',3',4',6'-hepta-O-acetyl--D-lactosyl)-L-serine, Benzyl Ester is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for the creation of a wide range of molecules with potential applications in different industries.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-Diphenylmethylene-O-(2,3,6,2',3',4',6'-hepta-O-acetyl--D-lactosyl)-L-serine, Benzyl Ester is used as a building block for the development of new drugs. Its chemical properties enable the creation of novel drug candidates with potential therapeutic applications.
3. Used in Chemical Research:
N-Diphenylmethylene-O-(2,3,6,2',3',4',6'-hepta-O-acetyl--D-lactosyl)-L-serine, Benzyl Ester is also used in chemical research to study the properties and reactivity of complex organic molecules. N-Diphenylmethylene-O-(2,3,6,2',3',4',6'-hepta-O-acetyl--D-lactosyl)-L-serine, Benzyl Ester can provide valuable insights into the behavior of similar structures and contribute to the advancement of organic chemistry.
4. Used in Material Science:
In the field of material science, N-Diphenylmethylene-O-(2,3,6,2',3',4',6'-hepta-O-acetyl--D-lactosyl)-L-serine, Benzyl Ester can be used to develop new materials with specific properties. Its unique structure may contribute to the creation of materials with enhanced performance in various applications, such as electronics, coatings, or adhesives.

Upstream product

• 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 
• 1013-88-3 Benzophenone imine 
• 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 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.