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

• 133-89-1 UDP-glucose 
• 108-98-5 thiophenol 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 121524-01-4 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside 
• 7296-15-3 alpha-D-mannopyranoside 
• 530-26-7 D-Mannose 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 13242-53-0 acetobromomannose 
• 17314-33-9 tributyltin phenyl sulfide 
• 83-87-4 D-Mannose pentaacetate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide 

Downstream Products

• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 27891-73-2 β-phenylsulfanyl lactoside 
• 97-30-3 methyl D-glucopyranoside 
• 62327-60-0 phenyl 2,3,4,6-tetra-O-methyl-1-thio-β-D-glucopyranoside 
• 21675-42-3 D-gluconic acid 
• 1208-20-4 S-phenyl benzenethiosulfinate 
• 709-50-2 methyl beta-D-glucopyranoside 
• 1198-69-2 D-glucono-1,4-lactone 
• 128848-50-0 phenyl 2,3,4,6-tetra-O-trimethylsilyl-1-thio-β-D-glucopyranoside 
• 124476-95-5 phenyl 2,3:4,6-di-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 145259-83-2 (2S,3R,4R,4aS,10aR)-6,6,8,8-Tetraisopropyl-2-phenylsulfanyl-hexahydro-1,5,7,9-tetraoxa-6,8-disila-benzocyclooctene-3,4-diol 
• 145259-84-3 Phenyl 2,3:4,6-bis-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-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 
• 210834-01-8 phenyl 6-O-trityl-1-thio-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.

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.