181629-33-4

Basic information

• Product Name: {(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
• Synonyms: {(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
• CAS NO: 181629-33-4
• Molecular Weight: 752.948
• Mol File: 181629-33-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: {(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(CAS DataBase Reference)
• NIST Chemistry Reference: {(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(181629-33-4)
• EPA Substance Registry System: {(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(181629-33-4)

Safety Data

• Hazardous Substances Data: 181629-33-4(Hazardous Substances Data)

Upstream product

• 15260-10-3 N-Boc-O-benzyl-L-threonine 
• 181629-25-4 2-(tri-O-benzyl-α-L-fucopyranosyl)ethylamine 
• 100-39-0 benzyl bromide 
• 145987-57-1 3,4,5-tri-O-acetyl-2,6-anhydro-1,7,8,9-tetradeoxy-L-glycero-D-galacto-non-8-enitol 
• 167990-42-3 3-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-propene 
• 181629-24-3 2-(tri-O-benzyl-α-L-fucopyranosyl)ethanol 
• 181786-26-5 3-(α-L-fucopyranosyl)-prop-1-ene 
• 64913-16-2 L-fucose tetraacetate 
• 181629-23-2 2-(tri-O-benzyl-α-L-fucopyranosyl)-acetaldehyde 

Downstream Products

• 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 

Relevant articles and documents

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.