190248-98-7

Basic information

• Product Name: ethyl 2,4-di-O-benzyl-1-thio-β-L-fucopyranoside
• Synonyms: ethyl 2,4-di-O-benzyl-1-thio-β-L-fucopyranoside
• CAS NO: 190248-98-7
• Molecular Weight: 388.528
• Mol File: 190248-98-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: ethyl 2,4-di-O-benzyl-1-thio-β-L-fucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2,4-di-O-benzyl-1-thio-β-L-fucopyranoside(190248-98-7)
• EPA Substance Registry System: ethyl 2,4-di-O-benzyl-1-thio-β-L-fucopyranoside(190248-98-7)

Safety Data

• Hazardous Substances Data: 190248-98-7(Hazardous Substances Data)

Upstream product

• 685109-95-9 ethyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside 
• 685109-92-6 ethyl 3-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 138343-55-2 ethyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 
• 138343-54-1 ethyl 3,4-di-O-isopropylidene-1-thio-β-L-fucopyranoside 
• 132799-10-1 ethyl 1-thio-α-L-fucopyranoside 
• 127501-41-1 ethyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside 
• 100-39-0 benzyl bromide 
• 138343-56-3 ethyl 2-O-benzyl-1-thio-β-L-fucopyranoside 
• 190248-97-6 (2R,3aR,4S,6R,7S,7aR)-7-Benzyloxy-6-ethylsulfanyl-4-methyl-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 

Downstream Products

• 190248-93-2 C₇₄H₉₁NO₁₇ 
• 190248-99-8 ethyl 2,4-di-O-benzyl-3,6-dideoxy-1-thio-β-L-xylo-hexopyranoside 
• 283587-81-5 Thiocarbonic acid O-[(2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-4-yl] ester O-pentafluorophenyl ester 
• 283587-78-0 octyl 3-O-acetyl-2,4-di-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 283587-79-1 octyl 2,4-di-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 283587-80-4 octyl 2,4-di-O-benzyl-3-O-methyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 283587-82-6 octyl 2,4-di-O-benzyl-α-L-xylo-hexopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 160243-28-7 ethyl 3-O-acetyl-2,4-di-O-benzyl-1-thio-β-L-fucopyranoside 

Relevant articles and documents

Synthesis of Fucosylated Chondroitin Sulfate Glycoclusters: A Robust Route to New Anticoagulant Agents

Fucosylated chondroitin sulfate (FuCS) is a structurally distinct glycosaminoglycan with excellent anticoagulant activity. Studies show that FuCS and its depolymerized fragments exhibit a different anticoagulant mechanism from that of heparin derivatives, with decreased risks of adverse effects and bleeding. However, further exploitation has been hindered by the scarcity of structurally defined oligosaccharides. Herein, facile method is reported for the synthesis of the repeating trisaccharide unit of FuCS based on the degradation of chondroitin sulfate polymers. A series of simplified FuCS glycomimetics that have highly tunable structures, controllable branches, and defined sulfation motifs were generated by copper-catalyzed alkyne–azide cycloaddition. Remarkable improvement in activated partial thromboplastin time (APTT) assay activities was observed as the branches increased, but no significant influences were observed for prothrombin time (PT) and thrombin time (TT) assay activities. Further FXase inhibition tests suggested that glycoclusters 33 b–40 b selectively inhibited intrinsic anticoagulant activities, but had little effect on the extrinsic and common coagulation pathways. Notably, glycoclusters with the 2,4-di-O-sulfated fucosyl residue displayed the most potency, which was in consistent with that of natural polysaccharides. These FuCS clusters demonstrated potency to mimic linear glycosaminoglycans and offer a new framework for the development of novel anticoagulant agents.

Synthesis and enzymatic evaluation of modified acceptors of recombinant blood group A and B glycosyltransferases

The disaccharide α-L-Fucp-(1→2)-β-D-Galp-(1→O)-Octyl (1) is an acceptor for the human blood group A and B glycosyltransferases. Seven analogues of 1, containing deoxy, methoxy and arabino modifications of the Fuc residue, were chemically synthesized and kinetically evaluated in radioactive enzymatic assays. Both the enzymes tolerate modification of the 3'-OH on the fucose residue. The 2'-OH was found to be key to the recognition of the acceptors by these enzymes. The arabino derivative was recognized as an acceptor by the A transferase (K(m) of 200 μM), but not the B transferase and is the first synthetic acceptor capable of distinguishing between the two enzyme activities. (C) 2000 Elsevier Science Ltd.