152015-42-4

Upstream product

• 138343-54-1 ethyl 3,4-di-O-isopropylidene-1-thio-β-L-fucopyranoside 
• 824-94-2 p-methoxybenzyl chloride 
• 132799-10-1 ethyl 1-thio-α-L-fucopyranoside 
• 127501-41-1 ethyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside 

Downstream Products

• 152015-44-6 Allyl O-<3,4-isopropylidene-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl>-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranoside 
• 283587-86-0 Thiocarbonic acid O-[(2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yl] ester O-pentafluorophenyl ester 
• 283587-83-7 octyl 3,4-di-O-benzyl-2-O-p-methoxybenzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 283587-84-8 octyl 3,4-di-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 283587-85-9 octyl 3,4-di-O-benzyl-2-O-methyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 283587-87-1 octyl 3,4-di-O-benzyl-α-L-xylo-hexopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 283587-71-3 ethyl 3,4-di-O-benzyl-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside 
• 418764-42-8 allyl (3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-(1->2)-3,6-di-O-p-methoxybenzyl-4-O-methyl-β-D-galactopyranoside 
• 418764-37-1 S-ethyl 3,4-di-O-acetyl-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside 
• 283587-70-2 ethyl 2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside 
• 213402-54-1 N-{(2R,3R,4R,5S,6R)-2-Allyloxy-4-hydroxy-6-(4-methoxy-benzyloxymethyl)-5-[(3aR,4S,6S,7S,7aR)-7-(4-methoxy-benzyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-tetrahydro-pyran-3-yl}-acetamide 
• 213402-36-9 N-{(2R,3R,4R,5S,6R)-2-Allyloxy-5-hydroxy-6-(4-methoxy-benzyloxymethyl)-4-[(3aR,4S,6S,7S,7aR)-7-(4-methoxy-benzyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-tetrahydro-pyran-3-yl}-acetamide 
• 213402-17-6 N-[(2R,4aR,6R,7R,8R,8aS)-6-Allyloxy-8-[(3aR,4S,6S,7S,7aR)-7-(4-methoxy-benzyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 
• 152015-43-5 Allyl O-<3,4-isopropylidene-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl>-(1->6)-2-acetamido-2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranoside 

Relevant academic research and scientific papers

Application and limitations of the methyl imidate protection strategy of N-acetylglucosamine for glycosylations at O-4: synthesis of Lewis A and Lewis X trisaccharide analogues

We describe here the synthesis of the allyl Lea trisaccharide antigen as well as that of an analogue of the Lex trisaccharide antigen, in which the galactose residue has been replaced by a glucose unit. Although successful fucosylations at O-4 of N-acetylglucosamine acceptors have been reported using perbenzylated thioethyl fucosyl donors under MeOTf activation, such conditions led in our case to the conversion of our acceptor to the corresponding alkyl imidates. Indeed, in this synthesis of the Lea analogue, we demonstrate that the temporary protection of the N-acetyl group as a methyl imidate is advantageous to fucosylate at O-4. In contrast, we report here that glucosylation at O-4 of an N-acetylglucosamine monosaccharide acceptor using the α-trichloroacetimidate of peracetylated glucopyranose as a donor proceeded in better yields under activation with excess BF3·OEt2 than that of the corresponding methyl imidate. Therefore, we conclude that activation of thioglycoside donors by MeOTf to glycosylate at O-4 of a glucosamine acceptor is best accomplished following the temporary protection of the N-acetyl group as a methyl imidate, especially when the donors are highly reactive and prone to degradation. In contrast, if donor and acceptor can withstand multiple equivalents of BF3·OEt2, glycosylations at O-4 of a glucosamine acceptor with a trichloroacetimidate donor does not benefit from the temporary protection of the N-acetyl group as a methyl imidate.

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.