936115-46-7

Upstream product

• 100-51-6 benzyl alcohol 
• 874-90-8 4-methoxybenzonitrile 
• 60022-62-0 L-serine benzyl ester hydrochloride 
• 5291-48-5 bis(4-methoxyphenyl)methanimine 
• 936115-45-6 benzyl N-bis(4-methoxyphenyl)methylene-L-serinate 
• 604-69-3 β-D-glucose pentaacetate 
• 1253053-57-4 C₂₅H₂₅NO₅ 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 801992-26-7 C₂₄H₃₁NO₁₂ 
• 118358-37-5 N-9-fluorenylmethoxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-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.

IMPROVED METHOD FOR MAKING AMINO ACID CLYCOSIDES AND GLYCOPEPTIDES

The invention relates to an improved method of preparing amino glycosides and glycopeptides. The method involves reacting an diarylketimine with an amino acid having a hydroxal side chain to produce an imino-bound intermediate compound. This intermediate is then reacted with an acetylated sugar residue under suitable conditions to yield amino glycoside. The synthetic amino glycoside may be incorporated into a peptide chain under conditions compatible with standard glycopeptide synthesis reactions.