181629-23-2

Upstream product

• 64913-16-2 L-fucose tetraacetate 
• 181786-26-5 3-(α-L-fucopyranosyl)-prop-1-ene 
• 145987-57-1 3,4,5-tri-O-acetyl-2,6-anhydro-1,7,8,9-tetradeoxy-L-glycero-D-galacto-non-8-enitol 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 100-39-0 benzyl bromide 
• 73-34-7 6-deoxy-L-galactose 
• 167990-42-3 3-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-propene 

Downstream Products

• 1217514-17-4 (E)-4-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-(thiazol-2-yl)-but-2-en-1-one 
• 181629-27-6 {(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]-propyl}-carbamic acid tert-butyl ester 
• 181629-33-4 {(1S,2R)-2-Benzyloxy-1-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylcarbamoyl]-propyl}-carbamic acid tert-butyl ester 
• 181629-37-8 (2S,3R)-2-Amino-3-benzyloxy-N-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-butyramide 
• 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 
• 186585-79-5 ((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}-propyl)-carbamic acid tert-butyl ester 
• 186585-89-7 Tetradecylcarbamoylmethyl-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-carbamic acid tert-butyl ester 
• 186585-76-2 N-Tetradecyl-2-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylamino]-acetamide 
• 186585-73-9 {tert-Butoxycarbonyl-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-amino}-acetic acid methyl ester 
• 186585-87-5 {tert-Butoxycarbonyl-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-amino}-acetic acid 
• 215163-55-6 (S)-2-[2-([1-Phenethylcarbamoyl-2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-{3-[4-(4-phenoxy-phenoxy)-phenyl]-propionyl}-amino)-acetylamino]-pentanedioic acid dibenzyl ester 
• 215163-56-7 N-((1S,2R)-1-{Benzyl-[1-(methoxycarbonylmethyl-carbamoyl)-2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-carbamoyl}-3-benzyloxy-2-hydroxy-propyl)-succinamic acid benzyl ester 
• 288629-16-3 2(S)-[(1(S)-phenylethyl)amino]-3-[2,3,4-tribenzyl-α-L-fucopyranosyl]propanenitrile 

Relevant academic research and scientific papers

Solid-phase supported mimic of GDP-l-galactose

A C-glycoside mimetic of l-galactose 1-diphosphate, a potential ligand of GDP-l-galactose hydrolase, an enzyme involved in the biosynthesis of vitamin C, has been designed, stereoselectively synthesised by C-allylation of tribenzylated l-fucose, by period

Design, synthesis and biological evaluation of aryl-substituted sialyl Lewis X mimetics prepared via cross-metathesis of C-fucopeptides

Several aryl substituted C-fucopeptides have been developed as sialyl Lewis X mimetics. Although the compounds have a much simpler structure compared to SLe(x), up to 3-times higher binding affinity toward E-selectin and >1000 times toward P-selectin was observed. Furthermore, a convenient strategy for generating a number of analogues from a SLe(x) mimetic template at a very late stage of the synthesis was introduced, using a ruthenium catalyzed cross olefin metathesis under benchtop conditions. Copyright (C) 1999 Elsevier Science Ltd.

Design and synthesis of C-linked fucosides as inhibitors of E-selectin

Two series of C-linked fucosides as mimetics for the tetrasaccharide sialyl Lewis X have been synthesized and tested as inhibitors of E-Selectin. The fucopeptides have been prepared from three key intermediates, including α-C-allyl fucose, natural and unnatural amino acids bearing hydroxyl groups and an α,ω-diacid moiety for the imitation of the essential three parts of SLe(x), i.e., the Fuc, Gal, and NeuAc. The nature and distance of the linkage of the fucose moiety to the amino acids as well as the distance between the amino acids and the terminal carboxylic acid group turned out to be crucial for the biological activity. In addition the necessity of both OH groups (4- and 6-OH) in the Gal part could be confirmed. Conformational NMR study of the most active mimetic supports the structure-activity relationship. A second series of mimetics was prepared, where Fuc and Gal moieties were purely C-linked. In the synthesis of β-C-allyl galactose an intramolecular 1,2-hydride shift led to an interesting side product. However, the substituted glycosidic oxygens led to a substantial loss of conformational constrain, which could not be compensated and resulted in low activity.

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.