98461-49-5

Basic information

• Product Name: phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside
• Synonyms: phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside
• CAS NO: 98461-49-5
• Molecular Weight: 368.408
• Mol File: 98461-49-5.mol

Chemical Properties

• CAS DataBase Reference: phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside(98461-49-5)
• EPA Substance Registry System: phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside(98461-49-5)

Safety Data

• Hazardous Substances Data: 98461-49-5(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 26905-22-6 hydroxymethyl phenyl sulfide 
• 869848-87-3 2,3,4-tri-O-acetyl-β-L-arabinopyranosyl trichloroacetimidate 
• 930-69-8 sodium thiophenolate 
• 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 
• 14227-90-8 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide 
• 158419-93-3 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl thiocyanate 
• 128376-91-0 2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate 
• 62446-93-9 1,2,3,4-tetra-O-acetyl-D-xylopyranose 
• 106820-14-8 2,3,4-Tri-O-acetyl-D-xylopyranose 
• 1233-03-0 α-D-xylopyranose tetraacetate 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 3068-31-3 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose 

Downstream Products

• 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 
• 1352718-30-9 C₁₁H₁₄O₄S 
• 1352718-31-0 C₃₂H₃₂O₄S 
• 1352717-86-2 2,3,4-tri-O-benzyl-β-L-arabinopyranosyl chloride 
• 1352718-46-7 methyl 2,3-di-O-methyl-4-O-(2,3,4-tri-O-benzyl-α-L-arabinopyranosyl)-α-D-glucopyranoside 
• 1352718-47-8 methyl 2,3-di-O-methyl-6-O-(2,3,4-tri-O-benzyl-α-L-arabinopyranosyl)-α-D-glucopyranoside 
• 18039-26-4 2,3,4-tri-O-benzyloxy-L-arabinopyranose 
• 442631-65-4 C₇₇H₁₁₆O₁₈Si₂ 
• 335197-29-0 C₇₇H₁₁₆O₁₈Si₂ 
• 335197-11-0 4-Methoxy-benzoic acid (2S,3R,4S,5R)-2-[(2S,3R,4R,5S)-3-acetoxy-2-(2,2,2-trichloro-acetimidoyloxy)-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester 

Relevant articles and documents

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.

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.

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.

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

In(III) triflate-mediated solvent-free synthesis and activation of thioglycosides by ball milling and structural analysis of long chain alkyl thioglycosides by TEM and quantum chemical methods

Conventional solution-phase synthesis of thioglycosides from glycosyl acetates and thiols in the presence of In(III) triflate as reported for benzyl thioglucoside failed when applied to the synthesis of phenolic and alkyl thioglycosides. But, it was achieved in high efficiency and diastereospecificity with ease by solvent-free grinding in a ball mill. The acetates in turn were also obtained by the homogenization of free sugars with stoichiometric amounts of acetic anhydride and catalytic In(OTf)3 in the mill as neat products. Per-O-benzylated thioglycosides on grinding with an acceptor sugar in the presence of In(OTf)3 yield the corresponding O-glycosides efficiently. The latter in the case of a difficult secondary alcohol was nearly exclusive (>98%) in 1,2-cis-selectivity. In contrast, the conventional methods for this purpose require use of a coreagent such as NIS along with the Lewis acid to help generate the electrophilic species that actually is responsible for the activation of the thioglycoside donor in situ. The distinctly different self-assembling features of the peracetylated octadecyl 1-thio-α- and β-d-galactopyranosides observed by TEM could be rationalized by molecular modeling.