16758-34-2

Basic information

• Product Name: PHENYL 1-THIO-BETA-D-GALACTOPYRANOSIDE
• Synonyms: PH-THIO-BETA-D-GAL;PHENYL 1-THIO-BETA-D-GALACTOPYRANOSIDE;PHENYL-BETA-D-THIOGALACTOPYRANOSIDE;PHENYL-BETA-D-THIOGALACTOSIDE;phenyl-B-D-thiogalactoside;Phenyl-B-D-ThiogalactopyranosideA.R.;.beta.-D-Galactopyranoside, phenyl 1-thio-;Phenylb-D-thiogalactopyranoside
• CAS NO: 16758-34-2
• Molecular Formula: C₁₂H₁₆O₅S
• Molecular Weight: 272.32
• EINECS: 240-818-7
• Product Categories: Carbohydrates;Carbohydrates & Derivatives;Sulfur & Selenium Compounds
• Mol File: 16758-34-2.mol
• Article Data: 140

Chemical Properties

• Melting Point: 88-91°C
• Boiling Point: 510.7 °C at 760 mmHg
• Flash Point: 262.6 °C
• Appearance: /
• Density: 1.48 g/cm³
• Vapor Pressure: 2.98E-11mmHg at 25°C
• Refractive Index: 1.667
• Storage Temp.: Refrigerator
• Solubility: Methanol (Slightly), Water (Very Slightly)
• PKA: 12.89±0.70(Predicted)
• CAS DataBase Reference: PHENYL 1-THIO-BETA-D-GALACTOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYL 1-THIO-BETA-D-GALACTOPYRANOSIDE(16758-34-2)
• EPA Substance Registry System: PHENYL 1-THIO-BETA-D-GALACTOPYRANOSIDE(16758-34-2)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 22-26-36-45
• WGK Germany: 3
• Hazardous Substances Data: 16758-34-2(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1/C12H16O5S/c13-6-8-9(14)10(15)11(16)12(17-8)18-7-4-2-1-3-5-7/h1-5,8-16H,6H2/t8-,9+,10+,11-,12+/m1/s1

Upstream product

• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 75-77-4 chloro-trimethyl-silane 
• 4551-15-9 phenylthiotrimethylsilane 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 17314-33-9 tributyltin phenyl sulfide 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 572-09-8 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-bromo-tetrahydro-pyran-4-yl ester 
• 108-98-5 thiophenol 
• 604-69-3 β-D-glucose pentaacetate 
• 492-61-5 β-D-glucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 
• 930-69-8 sodium thiophenolate 

Downstream Products

• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 71676-30-7 (2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 5346-81-6 phenyl 2,3,6-tri-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside 
• 71676-30-7 phenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 213998-04-0 phenyl 3,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside 
• 236115-71-2 6-(4-methylbenzenesulfonate)-phenyl-1-thio-β-D-glucopyranoside 
• 498-07-7 levoglucosan 
• 252001-14-2 (1R,3S,4R,4aR,9aR)-1-Hydroxymethyl-6,6,8,8-tetraisopropyl-3-phenylsulfanyl-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocyclohepten-4-ol 
• 273749-60-3 phenyl 4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside 
• 345197-64-0 1-phenylthio-1-deoxy-2,3,4,6-di-(O-isopropylidene)-β-D-glucopyranoside 

Relevant articles and documents

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.

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.

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.