24404-53-3

Usage

Uses

Used in Pharmaceutical Industry:
PHENYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GALACTOPYRANOSIDE is used as an intermediate for the preparation of nucleosides, which are essential components of DNA and RNA. These nucleosides play a crucial role in various biological processes, including the storage and transmission of genetic information, and are often targeted for therapeutic applications in the treatment of viral infections and cancer.
Used in Chemical Industry:
In the chemical industry, PHENYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GALACTOPYRANOSIDE can be utilized as a building block for the synthesis of various complex organic molecules. Its unique structure allows for further chemical modifications and functionalization, making it a valuable compound for the development of new materials and pharmaceuticals.

InChI:InChI=1/C20H24O9S/c1-11(21)25-10-16-17(26-12(2)22)18(27-13(3)23)19(28-14(4)24)20(29-16)30-15-8-6-5-7-9-15/h5-9,16-20H,10H2,1-4H3/t16-,17+,18+,19-,20+/m1/s1

Upstream product

• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 108-24-7 acetic anhydride 
• 108-98-5 thiophenol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 439-03-2 2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 145259-93-4 Phenyl 2,3-di-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1-thio-β-D-glucopyranoside 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 14365-16-3 bis-(phenylthio)-dibutylstannane 
• 604-68-2 α-D-glucopyranose peracetylate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 882-33-7 diphenyldisulfane 
• 2872-65-3 p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 83-87-4 D-glucose pentaacetate 

Downstream Products

• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 53438-23-6 phenylsulfonyl 2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-glucopyranoside 
• 172364-19-1 4-methylumbelliferyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1<*>3)-2-O-benzyl-4,6-benzylidene-β-D-glucopyranoside 
• 439-03-2 2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 3947-62-4 2,3,4,6-tetraacetylglucose 
• 211423-01-7 p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside 
• 124595-24-0 phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranoside 
• 794591-52-9 1-O-benzoyl-2,4-O-benzylidene-5,6-O-isopropylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-D-glucitol 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

Stereoselective O-Glycosylations by Pyrylium Salt Organocatalysis**

Despite many years of invention, the field of carbohydrate chemistry remains rather inaccessible to non-specialists, which limits the scientific impact and reach of the discoveries made in the field. Aiming to increase the availability of stereoselective

Total Synthesis of a Partial Structure from Arabinogalactan and Its Application for Allergy Prevention

Arabinogalactan, a microheterogeneous polysaccharide occurring in plants, is known for its allergy-protective activity, which could potentially be used for preventive allergy treatment. New treatment options are highly desirable, especially in a preventive manner, due to the constant rise of atopic diseases worldwide. The structural origin of the allergy-protective activity of arabinogalactan is, however, still unclear and isolation of the polysaccharide is not feasible for pharmaceutical applications due to a variation of the activity of the natural product and contaminations with endotoxins. Therefore, a pentasaccharide partial structure was selected for total synthesis and subsequently coupled to a carrier protein to form a neoglycoconjugate. The allergy-protective activity of arabinogalactan could be reproduced with the partial structure in subsequent in vivo experiments. This is the first example of a successful simplification of arabinogalactan with a single partial structure while retaining its allergy-preventive potential.

Rhamnogalacturonan II: Chemical Synthesis of a Substructure Including α-2,3-Linked Kdo**

The synthesis of a fully deprotected Kdo-containing rhamnogalacturonan II pentasaccharide is described. The strategy relies on the preparation of a suitably protected homogalacturonan tetrasaccharide backbone, through a post-glycosylation oxidation approach, and its stereoselective glycosylation with a Kdo fluoride donor.

Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions

A series of β-d-glucopyranosyl derivates have been synthesized and evaluated in photooxidation reactions promoted by visible light and mediated by organic dyes under aerobic conditions. Among the different photocatalysts employed, tetra-O-acetyl riboflavin afforded chemoselectively the respective sulfoxides, without over-oxidation to sulfones, in good to excellent yields and short reaction times. This new methodology for the preparation of synthetically useful glycosyl sulfoxides constitutes a catalytic, efficient, economical, and environmentally friendly oxidation process not reported so far for carbohydrates.

Reactivity–Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides

The assembly of complex bacterial glycans presenting rare structural motifs and cis-glycosidic linkages is significantly obstructed by the lack of knowledge of the reactivity of the constituting building blocks and the stereoselectivity of the reactions i

How do Various Reaction Parameters Influence Anomeric Selectivity in Chemical Glycosylation with Thioglycosides and NIS/TfOH Activation?

The reaction of glycosyl donor phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside with NIS/TfOH(cat.) was systematically studied under various reaction conditions. Neither the molecular sieve pore size nor amount of NIS activator was found to have a

Chemical Synthesis and Biological Evaluations of Adiponectin Collagenous Domain Glycoforms

The homogeneously glycosylated 76-amino acid adiponectin collagenous domains (ACDs) with all of the possible 15 glycoforms have been chemically and individually synthesized using stereoselective glycan synthesis and chemical peptide ligation. The following biological and pharmacological studies enabled correlating glycan pattern to function in the inhibition of cancer cell growth as well as the regulation of systemic energy metabolism. In particular, hAdn-WM6877 was tested in detail with different mouse models and it exhibited promising in vivo antitumor, insulin sensitizing, and hepatoprotective activities. Our studies demonstrated the possibility of using synthetic glycopeptides as the adiponectin downsized mimetic for the development of novel therapeutics to treat diseases associated with deficient adiponectin.

Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride

This study describes a new convenient method for the photocatalytic generation of glycosyl fluorides using sulfur(VI) hexafluoride as an inexpensive and safe fluorinating agent and 4,4′-dimethoxybenzophenone as a readily available organic photocatalyst. This mild method was employed to generate 16 different glycosyl fluorides, including the substrates with acid and base labile functionalities, in yields of 43%-97%, and it was applied in continuous flow to accomplish fluorination on an 7.7 g scale and 93% yield.

Fighting Shigella by Blocking Its Disease-Causing Toxin

Shiga toxin is an AB5 toxin produced by Shigella species, while related toxins are produced by Shiga toxin-producing Escherichia coli (STEC). Infection by Shigella can lead to bloody diarrhea followed by the often fatal hemolytic uremic syndrome (HUS). In the present paper, we aimed for a simple and effective toxin inhibitor by comparing three classes of carbohydrate-based inhibitors: glycodendrimers, glycopolymers, and oligosaccharides. We observed a clear enhancement in potency for multivalent inhibitors, with the divalent and tetravalent compounds inhibiting in the millimolar and micromolar range, respectively. However, the polymeric inhibitor based on galabiose was the most potent in the series exhibiting nanomolar inhibition. Alginate and chitosan oligosaccharides also inhibit Shiga toxin and may be used as a prophylactic drug during shigella outbreaks.

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.