23661-28-1

Basic information

• Product Name: PHENYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE
• Synonyms: PHENYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE;PHENYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BET;.beta.-D-Glucopyranoside, phenyl 1-thio-, tetraacetate;1-phenyl-1-thio-β-d-glucopyranoside tetraacetate;Phenyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside;PHENYL-2,3,4,6-TETRA-O-ACETYL-1-THIO-SS-D-GLUCOPYRANOSIDE;Phenyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosid;Phenyl 2,3,4,6-O-Tetraacetyl-1-thio-β-D-glucopyranoside
• CAS NO: 23661-28-1
• Molecular Formula: C₂₀H₂₄O₉S
• Molecular Weight: 440.46
• Product Categories: Biochemistry;Glucose;Glycosyl Donors;Sugars;Thioglycosides;Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis;Carbohydrates
• Mol File: 23661-28-1.mol
• Article Data: 177

Chemical Properties

• Melting Point: 116-119 °C(lit.)
• Boiling Point: 514.6 °C at 760 mmHg
• Flash Point: 247.6 °C
• Appearance: White to Off-white/Powder
• Density: 1.31 g/cm³
• Vapor Pressure: 1.06E-10mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: Freezer
• Solubility: slightly sol. in Chloroform
• CAS DataBase Reference: PHENYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE(23661-28-1)
• EPA Substance Registry System: PHENYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE(23661-28-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 23661-28-1(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

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

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 
• 127066-70-0 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl thiocyanate 
• 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 
• 930-69-8 sodium thiophenolate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 882-33-7 diphenyldisulfane 

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 
• 13992-15-9 phenyl-1-thio-α-D-glucopyranoside 
• 107961-09-1 α-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,4,6-tetra-O-acetyl-D-galactopyranose 
• 107961-09-1 β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 108681-43-2 phenylsulfonyl 2,3,4,6-tetra-O-acetyl-1-deoxy-α-D-mannopyranoside 
• 2936-70-1 (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 2823-44-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 28244-97-5 phenyl-1-thio-α-D-galactopyranoside 
• 604-70-6 tetra-O-acetyl-1-O-methyl-β-D-glucopyranose 
• 74808-17-6 methyl 6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 107961-09-1 α-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,4,6-tetra-O-acetyl-D-glucopyranose 
• 100432-86-8 1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 

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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.