196397-59-8

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 127061-11-4 phenyl 1-thio-α/β-L-fucopyranoside 
• 73-34-7 6-deoxy-L-galactose 
• 167612-34-2 phenyl 6-deoxy-2,3,4-tri-O-acetyl-1-thio-β-L-galactopyranoside 
• 187233-24-5 phenyl 6-deoxy-1-thio-β-L-galactopyranoside 
• 108-98-5 thiophenol 
• 116-11-0 2-Methoxypropene 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 16741-27-8 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide 
• 127061-10-3 phenyl 2,3,4-tri-O-acetyl-1-thio-L-fucopyranoside 
• 67-64-1 acetone 
• 75-77-4 chloro-trimethyl-silane 
• 16029-98-4 trimethylsilyl iodide 

Downstream Products

• 196397-63-4 phenyl 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside 
• 848416-65-9 phenyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 
• 1250436-25-9 phenyl 2-O-(4-methylbenzyl)-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 
• 1334671-92-9 phenyl 2-O-allyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 
• 1334671-96-3 phenyl 4-O-acetyl-2-O-allyl-3-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside 
• 1334671-94-1 phenyl 2-O-allyl-1-thio-β-L-fucopyranoside 
• 1250436-23-7 phenyl 3,4-di-O-benzoyl-2-O-benzyl-1-thio-β-L-fucopyranoside 
• 1250436-26-0 phenyl 2-O-(4-methylbenzyl)-1-thio-β-L-fucopyranoside 
• 1250436-27-1 phenyl 3,4-di-O-benzoyl-2-O-(4-methylbenzyl)-1-thio-β-L-fucopyranoside 
• 1013427-84-3 phenyl 3,4-O-isopropylidene-2-O-methylxanthogenato-1-thio-β-L-fucopyranoside 
• 261374-37-2 phenyl 4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-1-thio-β-L-fucopyranoside 
• 261374-33-8 phenyl 2-O-methyl-1-thio-β-L-fucopyranoside 
• 261374-35-0 phenyl 2,3-di-O-methyl-1-thio-β-L-fucopyranoside 
• 578738-08-6 phenyl 2,6-di-O-benzoyl-4-O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-3-O-[3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl]-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Total synthesis of trifluorobutyryl-modified, protected sialyl Lewis X by a convergent [2+2] approach

Structural and quantitative changes in the expression of sialic acid residues on the surface of eukaryotic cells profoundly influence a broad range of biological processes including inflammation, antigen recognition, microbial attachment and tumour metastasis. Uptake and incorporation of sialic acid analogues in mammalian cells enable structure-function studies and perturbation of specific recognition events. Our group has recently shown that a trifluorobutyryl-modified sialic acid metabolite diminishes the adhesion of mammalian cells to E and P-Selectin, presumably by leading to the expression of fluorinated sLex epitopes on cell surfaces, and interfering with the sLex-selectin interactions that are well known in mediating tumour cell migration (J. Med. Chem. 2010, 53, 4277). For studies directed towards understanding the molecular basis of this reduced adhesion, chemical synthesis of trifluorobutyrylated sialyl Lewis X (C4F3-sLex) was crucial. We have developed a highly efficient [2+2] approach for the assembly of C4F3-sLex on a preparative scale that contains versatile protective groups allowing the glycan to be surface immobilized or solubilized as needed for biophysical studies to investigate selectin interactions. This strategy can, in principle, be used for preparation of other N-modified sLex analogues.

METHOD FOR THE SYNTHESIS OF A TRISACCHARIDE

The present invention relates to an improved synthesis of a trisaccharide of the formula (1), novel intermediates used in the synthesis and the preparation of the intermediates.

NOVEL METHOD FOR THE SYNTHESIS OF A TRISACCHARIDE

The present invention relates to an improved synthesis of a trisaccharide of the formula, novel intermediates used in the synthesis and the preparation of the intermediates.

Synthesis of an O-sulfo LewisX analog as glycolipid antigen

The title compound containing dihydroceramide as a ligand for CD1d was accomplished using the mannosyl, glucosaminyl, and fucosyl donors, and a sphinganine analogue, as suitable building blocks. The 2-O-unprotected mannosyl donor was coupled effectively w

SYNTHESIS OF 2'-O-FUCOSYLLACTOSE

The present invention relates to an improved synthesis of a trisaccharide of the formula (1), novel intermediates used in the synthesis and the preparation of the intermediates.

SYNTHESIS OF 2 ' -O-FUCOSYLLACTOSE

The present invention relates to an improved synthesis of a trisaccharide of the formula, novel intermediates used in the synthesis and the preparation of the intermediates.

Synthesis of fully protected α-l-fucopyranosyl-(1→2)-β-d- galactopyranosides with a single free hydroxy group at position 2′, 3′ or 4′ using O-(2-naphthyl)methyl (NAP) ether as a temporary protecting group

Perbenzylated methyl α-l-fucopyranosyl-(1→2)-β-d- galactopyranosides having a single free OH group at position C-2′, C-3′ or C-4′ have been synthesized. Methyl 3,4,6-tri-O-benzyl- β-d-galactopyranoside was glycosylated either with phenyl 3,4-di-O-benzyl-2

Synthesis of Lewis X trisaccharide analogues in which glucose and rhamnose replace N-acetylglucosamine and fucose, respectively

Two analogues of the Lex trisaccharide, α-L-Fucp-(1→3)-[β-D-Galp-(1→4)]-D-Glcp were synthesized as allyl glycosides. In these derivatives either only the N-acetylglucosamine is replaced by glucose or both the N-acetylglucosamine and the fucosyl residue are replaced by glucose and rhamnose, respectively. Our synthetic scheme used armed β-thiophenyl fuco- and rhamnoside glycosyl donors that were prepared anomerically pure from the corresponding α-glycosyl bromides. The protecting groups were chosen to allow access to the fully deprotected trisaccharides without reduction of the allyl glycosidic group. These analogues will be used as soluble antigens in binding experiments with anti-Lex antibodies and can also be conjugated to a carrier protein and used as immunogens. In the course of this synthetic work, we also describe the use of reversed-phase HPLC to purify key protected trisaccharide intermediates prior to their deprotection.

Stereocontrolled elaboration of natural (-)-polycavernoside A, a powerfully toxic metabolite of the red alga Polycavernosa tsudai

A stereoselective total synthesis of natural levorotatory polycavernoside A (1) has been achieved. Initial investigations produced the properly activated disaccharide unit 18b via the conjoining of building blocks originating from L-fucose and D-xylose. T

Stereoselective synthesis of carba- and C-glycosyl analogs of fucopyranosides

Fucopyranoside analogs with methylene groups instead of endo- or exo- anomeric oxygens, carba- and C-fucopyranosides, respectively, were synthesized. For the synthesis of 5a-carba-L-fucose (1) two approaches were studied, which shared a common cyclitol bu