104253-38-5

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 54322-10-0 glutaric acid monobenzyl ester 
• 108-55-4 glutaric anhydride, 
• 100-51-6 benzyl alcohol 

Downstream Products

• 178271-90-4 4-(1-Carboxy-2-hydroxy-1-hydroxymethyl-ethylcarbamoyl)-butyric acid benzyl ester 
• 178272-04-3 4-((S)-2-Benzyloxy-1-carboxy-ethylcarbamoyl)-butyric acid benzyl ester 
• 182075-77-0 (2S,3R)-4-Benzyloxy-2-(4-benzyloxycarbonyl-butyrylamino)-3-hydroxy-butyric acid 
• 186585-61-5 4-{(1S,2R)-3-Benzyloxy-2-hydroxy-1-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylcarbamoyl]-propylcarbamoyl}-butyric acid benzyl ester 
• 186585-64-8 4-{(1S,2S)-4-Benzyloxy-2-hydroxy-1-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylcarbamoyl]-butylcarbamoyl}-butyric acid benzyl ester 
• 186585-82-0 4-((1S,2R)-3-Benzyloxy-2-hydroxy-1-{tetradecylcarbamoylmethyl-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-carbamoyl}-propylcarbamoyl)-butyric acid benzyl ester 
• 189071-41-8 4-{(S)-2-Benzyloxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-ethylcarbamoyl}-butyric acid benzyl ester 

Relevant academic research and scientific papers

Synthesis of sialyl Lewis X mimetics: Use of O-α-fucosyl-(1R, 2R)-2-aminocyclohexanol as core structure

Six glycopeptides containing O-α-fucosyl-(1R, 2R)-2-aminocyclohexanol were designed and prepared as sialyl Lewis X mimetics. Compounds 2 and 6 showed better binding affinities than SLe(X) (IC50 = 0.5 mM) to E-selectin with IC50 values of 0.4 and 0.2 mM respectively.

C-fucopeptides as selectin antagonists: Attachment of lipid moieties enhances the activity

The biological activity of a potent selectin antagonist could be 40-fold enhanced by attachment of a lipid moiety. Also an enantioselective synthesis of β,ω-dihydroxyamino acids by Sharpless asymmetric dihydroxylation (AD-reaction) allowed general access to this important class of compounds. Copyright (C) 1996 Elsevier Science Ltd.

Synthesis of sialyl Lewis X mimetics and related structures using the glycosyl phosphite methodology and evaluation of E-selectin inhibition

This paper describes our recent study of glycosyl phosphites for glycosylation reactions, with particular emphasis on the investigation of protecting group and stereochemistry effects on the anomeric reactivity and stereoselectivity, and the application of this methodology to the synthesis of Lewis X (Le(x)), Lewis Y (Le(y)), glycopeptides, and sialyl Lewis X (SLe(x)) mimetics. Both α-O-fucosyl-L-threonine and α-O-fucosyl-(1R,2R)-2-aminocyclohexanol were found to be effective templates for the chemical/enzymatic synthesis of SLe(x) mimetics, and some fucopeptides prepared were 5-10 times more active than SLe(x) as inhibitors of E-selectin.