98461-49-5

Upstream product

• 3111-52-2 potassium thiophenolate 
• 3068-29-9 2,3,4-tri-O-acetyl-β-D-arabinosyl bromide 
• 108-98-5 thiophenol 
• 108646-05-5 (3S,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 
• 3068-31-3 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 62446-93-9 1,2,3,4-tetra-O-acetyl-D-xylopyranose 
• 1233-03-0 α-D-xylopyranose tetraacetate 
• 106820-14-8 2,3,4-Tri-O-acetyl-D-xylopyranose 
• 158419-93-3 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl thiocyanate 
• 1233-03-0 1,2,3,4-tetra-O-acetyl-L-arabinopyranose 
• 1233-03-0 1,2,3,4-tetra-O-acetyl-α-L-arabinopyranose 
• 10369-25-2 2,3,4-tri-O-acetyl-α,β-L-arabinopyranose 
• 26905-22-6 hydroxymethyl phenyl sulfide 

Downstream Products

• 107961-12-6 β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,4-tri-O-acetyl-D-arabinopyranose 
• 20452-28-2 phenyl 1-thio-β-D-xylopyranoside 
• 303153-45-9 4-azido-2-O-benzoyl-4,6-dideoxy-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-galactopyranosyl fluoride 
• 144683-66-9 (2S,3R,4S,5R,6R)-2-((3R,4R,5R,6S)-4,5-Dihydroxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 144683-65-8 (2S,3R,4S,5R,6R)-2-((2S,3R,4S,5R)-3,5-Dihydroxy-2-phenylsulfanyl-tetrahydro-pyran-4-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 1007852-62-1 C₃₁H₃₃FO₁₃ 
• 1007855-12-0 2,4-di-O-benzoyl-6-deoxy-3-O-(2,3,4-tri-O-acetyl-α-D-xylopyranosyl)-α-D-galactopyranosyl fluoride 
• 870096-05-2 (2S,3R,4S,5R)-3,4,5-trimethoxy-2-(phenylthio)tetrahydro-2H-pyran 
• 131771-66-9 phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-xylopyranoside 

Relevant academic research and scientific papers

Chloromethyl Glycosides as Versatile Synthons to Prepare Glycosyloxymethyl-Prodrugs

This work investigates the addition of monosaccharides to marketed drugs to improve their pharmacokinetic properties for oral absorption. To this end, a set of chloromethyl glycoside synthons were developed to prepare a variety of glycosyloxymethyl-prodrugs derived from 5-fluorouracil, thioguanine, propofol and losartan. Drug release was studied in vitro using β-glucosidase confirming rapid conversion of the monosaccharide prodrugs to release the parent drug, formaldehyde and the monosaccharide. To showcase this prodrug approach, a glucosyloxymethyl conjugate of the tetrazole-containing drug losartan was used for in vivo experiments and showed complete release of the drug in a dog-model.

Carbohydrate-Based NK1R Antagonists with Broad-Spectrum Anticancer Activity

NK1R antagonists, investigated for the treatment of several pathologies, have shown encouraging results in the treatment of several cancers. In the present study, we report on the synthesis of carbohydrate-based NK1R antagonists and their evaluation as anticancer agents against a wide range of cancer cells. All of the prepared compounds, derived from either-arabinose, have shown high affinity and NK1R antagonistic activity with a broad-spectrum anticancer activity and an important selectivity, comparable to Cisplatin. This strategy has allowed us to identify the galactosyl derivative 14α , as an interesting hit exhibiting significant NK1R antagonist effect (kinact0.209 ± 0.103 μM) and high binding affinity for NK1R (IC50= 50.4 nM,Ki= 22.4 nM by measuring the displacement of [125I] SP from NK1R). Interestingly, this galactosyl derivative has shown marked selective cytotoxic activity against 12 different types of cancer cell lines.

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.

Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

ANTAGONISTS OF NK1 RECEPTORS DERIVED FROM CARBOHYDRATES, PRODUCTION METHOD AND MEDICAL USE

The invention relates to a compound of general formula (I), and to the use thereof in medicine, or for the production of a medicament for the treatment of different diseases, preferably a cancer such as melanoma, lung carcinoma or breast cancer. For this purpose, the invention also relates to a pharmaceutical composition comprising said compound. In addition, the invention relates to a method for producing the compound of general formula (I).

Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI3

Thioglycosylation of 1-hydroxyl glycosides catalyzed by in situ-generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per-modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation, high anomeric diastereoselectivity, and mild reaction conditions.

Efficient one-pot per-: O -acetylation-thioglycosidation of native sugars, 4,6- O -arylidenation and one-pot 4,6- O -benzylidenation-acetylation of S -/ O -glycosides catalyzed by Mg(OTf)2

A sequential one-pot per-O-acetylation-S-/O-glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6-O-arylidenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)2 to produce the corresponding 4,6-O-arylidenated product in high yields. Mg(OTf)2 can also mediate sequential one-pot benzylidenation-acetylation of mono and disaccharide based glycosides and thioglycosides in high yield.

Atom-Economical Dimerization Strategy by the Rhodium-Catalyzed Addition of Carboxylic Acids to Allenes: Protecting-Group-Free Synthesis of Clavosolide A and Late-Stage Modification

Natural products of polyketide origin with a high level of symmetry, in particular C2-symmetric diolides as a special macrolactone-based product class, often possess a broad spectrum of biological activity. An efficient route to this important

Carbohydrate-derived iminium salt organocatalysts for the asymmetric epoxidation of alkenes

A new family of carbohydrate-based dihydroisoquinolinium salts has been prepared and tested for potential as asymmetric catalysts for the epoxidation of unfunctionalized alkene substrates, providing up to 57% ee in the product epoxides.