2936-70-1

Basic information

• Product Name: PHENYL-BETA-D-THIOGLUCOPYRANOSIDE
• Synonyms: PH-THIO-BETA-D-GLC;PHENYL-BETA-D-THIOGLUCOPYRANOSIDE;PHENYL-BETA-D-THIOGLUCOSIDE;Phenylb-D-thioglucopyranoside;PHENYL-SS-D-THIOGLUCOPYRANOSIDE;Phenyl-β-D-thio-glucopyranosid;Phenyl β-D-thioglucopyranoside;phenyl 1-thiohexopyranoside
• CAS NO: 2936-70-1
• Molecular Formula: C₁₂H₁₆O₅S
• Molecular Weight: 272.32
• EINECS: 1533716-785-6
• Product Categories: Carbohydrates;substrate
• Mol File: 2936-70-1.mol
• Article Data: 96

Chemical Properties

• Melting Point: 135℃
• 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.: ?20°C
• Solubility: Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: PHENYL-BETA-D-THIOGLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYL-BETA-D-THIOGLUCOPYRANOSIDE(2936-70-1)
• EPA Substance Registry System: PHENYL-BETA-D-THIOGLUCOPYRANOSIDE(2936-70-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 2936-70-1(Hazardous Substances Data)

Usage

Uses

Phenyl β-D-Thioglucopyranoside is used as a reagent for dialkoxytriazine-type glycosyl donors for cellulase-catalyzed lactosylation in preparation of oligosaccharides.

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

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 4551-15-9 phenylthiotrimethylsilane 
• 17314-33-9 tributyltin phenyl sulfide 
• 572-09-8 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-bromo-tetrahydro-pyran-4-yl ester 
• 60619-58-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 121524-01-4 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside 
• 108-98-5 thiophenol 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 530-26-7 D-Mannose 
• 83-87-4 β-D-mannopyranose pentaacetate 

Downstream Products

• 262605-68-5 phenyl 6-O-triphenylmethyl-1-thio-α-D-mannopyranoside 
• 498-07-7 levoglucosan 
• 310870-40-7 phenyl 6-O-[(tert-butyl)diphenylsilyl]-1-thio-α-D-mannopyranoside 
• 345197-64-0 1-phenylthio-1-deoxy-2,3,4,6-di-(O-isopropylidene)-β-D-glucopyranoside 
• 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 
• 863998-40-7 phenyl 3,6-di-O-acetyl-1-thio-β-D-allopyranoside 
• 159407-19-9 phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 152488-25-0 phenyl 6-O-(tert-butyldimethylsilyloxy)-1-thio-α-D-mannopyranoside 
• 492-61-5 β-D-glucose 
• 492-62-6 alpha-D-glucopyranose 
• 210834-01-8 phenyl 6-O-trityl-1-thio-β-D-glucopyranoside 
• 62327-60-0 phenyl 2,3,4,6-tetra-O-methyl-1-thio-β-D-glucopyranoside 
• 161976-09-6 phenyl (2,3,4,6-tetra-O-acetyl-β-D-galacto-pyranosyl)-(1->6)-2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranoside 
• 270075-72-4 phenyl 1-thio-3,4-O-isopropylidene-6-O-(1-methoxyl-1-methylethyl)-β-D-galactopyranoside 

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.

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.

Leveraging Trifluoromethylated Benzyl Groups toward the Highly 1,2- Cis-Selective Glucosylation of Reactive Alcohols

Here, we demonstrate that substitution of the benzyl groups of glucosyl imidate donors with trifluoromethyl results in a substantial increase in 1,2-cis-selectivity when activated with TMS-I in the presence of triphenylphosphine oxide. Stereoselectivity is dependent on the number of trifluoromethyl groups (4-trifluoromethylbenzyl vs 3,5-bis-trifluoromethylbenzyl). Particularly encouraging is that we observe high 1,2-cis-selectivity with reactive alcohol acceptors.