138343-56-3

Basic information

• Product Name: ethyl 2-O-benzyl-1-thio-β-L-fucopyranoside
• Synonyms: ethyl 2-O-benzyl-1-thio-β-L-fucopyranoside
• CAS NO: 138343-56-3
• Molecular Weight: 298.403
• Mol File: 138343-56-3.mol

Chemical Properties

• CAS DataBase Reference: ethyl 2-O-benzyl-1-thio-β-L-fucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-O-benzyl-1-thio-β-L-fucopyranoside(138343-56-3)
• EPA Substance Registry System: ethyl 2-O-benzyl-1-thio-β-L-fucopyranoside(138343-56-3)

Safety Data

• Hazardous Substances Data: 138343-56-3(Hazardous Substances Data)

Upstream product

• 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 
• 138343-55-2 ethyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 

Downstream Products

• 1337979-63-1 8-ethoxycarbonyloctyl 3,4-di-O-benzoyl-2-O-benzyl-β-L-fucopyranoside 
• 1337979-64-2 8-ethoxycarbonyloctyl 3,4-di-O-benzoyl-2-O-benzyl-α-L-fucopyranoside 
• 1337979-74-4 methyl 3,4-di-O-benzoyl-2-O-benzyl-β-L-fucopyranosyl-(1->2)-3-O-benzyl-4,6-O-benylidene-α-D-galactopyranoside 
• 1363732-67-5 methyl 3,4-di-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl-(1->2)-3-O-benzyl-4,6-O-benylidene-α-D-galactopyranoside 
• 1337979-71-1 decyl 3,4-di-O-benzoyl-2-O-benzyl-β-L-fucopyranoside 
• 1337979-72-2 decyl 3,4-di-O-benzoyl-2-O-benzyl-α-L-fucopyranoside 
• 1337979-61-9 ethyl 3,4-di-O-benzoyl-2-O-benzyl-1-thio-β-L-fucopyranoside 
• 160243-09-4 ethyl 4-O-benzoyl-2-O-benzyl-3-O-chloroacetyl-1-thio-β-L-fucopyranoside 
• 283587-76-8 Thiocarbonic acid O-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl] ester O-pentafluorophenyl ester 
• 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 
• 283587-73-5 octyl 4-O-acetyl-2,3-di-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 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 
• 283587-74-6 octyl 2,3-di-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside 

Relevant articles and documents

A Single Route to Mammalian N-Glycans Substituted with Core Fucose and Bisecting GlcNAc

The occurrence of α1,6-linked core fucose on the N-glycans of mammalian glycoproteins is involved in tumor progression and reduces the bioactivity of antibodies in antibody-dependent cell-mediated cytotoxicity (ADCC). Since core-fucosylated N-glycans are difficult to isolate from natural sources, only chemical or enzymatic synthesis can provide the desired compounds for biological studies. A general drawback of chemical α-fucosylation is that the chemical assembly of α1,6-linked fucosides is not stereospecific. A robust and general method for the α-selective fucosylation of acceptors with primary hydroxy groups in α/β ratios exceeding 99:1 was developed. The high selectivities result from the interplay of an optimized protecting group pattern of the fucosyl donors in combination with the activation principle and the reaction conditions. Selective deprotection yielded versatile azides of all mammalian complex-type core-fucosylated N-glycans with 2-4 antennae and optional bisecting GlcNAc.

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.