167612-34-2

Upstream product

• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 108-98-5 thiophenol 
• 16741-27-8 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide 
• 882-33-7 diphenyldisulfane 
• 64913-16-2 L-fucose tetraacetate 
• 28915-80-2 2,3,4-tri-O-acetyl-L-fucopyranose 
• 930-69-8 sodium thiophenolate 
• 75247-29-9 (2R,3S,4R,5R,6S)-2-bromo-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 73-34-7 6-deoxy-L-galactose 
• 108-24-7 acetic anhydride 

Downstream Products

• 196397-59-8 phenyl 3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 
• 196397-63-4 phenyl 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside 
• 578738-14-4 C₅₇H₆₂O₂₀ 
• 578738-09-7 allyl 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]-β-D-glucopyranoside 
• 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 
• 187233-24-5 phenyl 6-deoxy-1-thio-β-L-galactopyranoside 
• 1250831-09-4 Phenyl 2,3,4-tri-O-(2,4,6-trimethylbenzyl)-1-thio-β-L-fucopyranoside 
• 1250831-08-3 phenyl 2,3,4-tri-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 
• 1250436-26-0 phenyl 2-O-(4-methylbenzyl)-1-thio-β-L-fucopyranoside 
• 1250436-25-9 phenyl 2-O-(4-methylbenzyl)-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 
• 1250436-23-7 phenyl 3,4-di-O-benzoyl-2-O-benzyl-1-thio-β-L-fucopyranoside 
• 848416-65-9 phenyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 
• 167612-35-3 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 

Relevant academic research and scientific papers

Supramolecular scaffolds on glass slides as sugar based rewritable sensors for bacteria

We describe here the sugar functionalized β-cyclodextrin-ferrocene glass slides as fully reversible bacterial biosensors under the influence of external adamantane carboxylic acid. The prototype d-mannose-E. coli ORN 178 and l-fucose-P. aeruginosa interactions serve as a model to illustrate the new approach.

Concise Synthesis of 1-Thioalkyl Glycoside Donors by Reaction of Per-O-acetylated Sugars with Sodium Alkanethiolates under Solvent-Free Conditions

A relatively green method for synthesizing 1-thioalkyl glycosides has been developed, where sodium alkanethiolates were used to react with per-O-acetylated sugars instead of odorous alkyl mercaptans in the presence of BF3·Et2O without the use of solvents under mild conditions. Furthermore, we found that 1,2-trans-β-thioglycosides can be converted into corresponding 1,2-cis-α-thioglycosides in the presence of trifluoromethanesulfonic acid in nonpolar solvents under mild conditions. This provides a simple and efficient new approach for synthesizing challenging 1,2-cis-α-thioglycosides.

An efficient synthetic route to O-(2-O-benzyl-3,4-di-O-acetyl-α/β-L-fucopyranosyl)-trichloroacetimidate

An efficient synthetic route to prepare O-(2-O-benzyl-3,4-di-O-acetyl-α/β-L-fucopyranosyl)-trichloroacetimidate from L-fucose was developed by introducing the thiophenyl group at the anomeric center and the benzylidene functional group to protect the 3 an

Kilogram scale chemical synthesis of 2′-fucosyllactose

A scalable synthetic procedure to high quality 2′-fucosyllactose, the most abundant oligosaccharide in human breast milk, has been designed and validated in kilogram scale. The synthetic route has been developed to suit industrial environment and contains

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.

Gram-scale synthesis of an armed colitose thioglycoside

A concise gram-scale synthesis of protected colitose thioglycosides for use in bacterial carbohydrate antigen synthesis is described. The synthesis proceeds in six steps and 59-70% overall yield from commercially available L-fucose, making it the most eff

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.

Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols

A series of glycosyl hemiacetal derivatives have been transformed into thioglycosides and glycosyl thiols in a one-pot two-step reaction sequence mediated by Appel reagent (carbon tetrabromide and triphenylphosphine). 1,2-trans-Thioglycosides and β-glycosyl thiol derivatives were stereoselectively formed by the reaction of the in situ generated glycosyl bromides with thiols and sodium carbonotrithioate. The reaction conditions are reasonably simple and yields were very good.

Polymethylhydrosiloxane (PMHS): A convenient option for synthetic applications of the iodine/silane combined reagent - Straightforward entries to 2-hydroxyglycals and useful building-blocks of glucuronic acid and glucosamine

Polymethylhydrosiloxane (PMHS) proved to be a practically convenient alternative to triethylsilane in a large set of synthetic elaborations entailing the quick generation of glycosyl iodides with a iodine/silane combined reagent. In addition, the scope of this combined reagent was expanded to the especially fast generation of 2-acetoxyglycals, and the rapid synthesis of useful building-blocks of D-glucuronic acids and D-glucosamine. All the synthetic targets were obtained in especially short times either via one-pot procedures or through experimental sequences devoid of laborious chromatographical purifications of intermediates. Polymethylhydrosiloxane (PMHS) is a practically convenient alternative to triethylsilane in a large set of synthetic elaborations entailing the quick generation of glycosyl iodides with a iodine/silane combined reagent. Copyright

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.