13992-15-9

Basic information

• Product Name: .alpha.-D-Glucopyranoside, phenyl 1-thio-
• Synonyms: .alpha.-D-Glucopyranoside, phenyl 1-thio-
• CAS NO: 13992-15-9
• Molecular Formula: C₁₂H₁₆O₅S
• Molecular Weight: 0
• Mol File: 13992-15-9.mol
• Article Data: 98

Chemical Properties

• Appearance: /
• CAS DataBase Reference: .alpha.-D-Glucopyranoside, phenyl 1-thio-(CAS DataBase Reference)
• NIST Chemistry Reference: .alpha.-D-Glucopyranoside, phenyl 1-thio-(13992-15-9)
• EPA Substance Registry System: .alpha.-D-Glucopyranoside, phenyl 1-thio-(13992-15-9)

Safety Data

• Hazardous Substances Data: 13992-15-9(Hazardous Substances Data)

Upstream product

• 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 
• 133-89-1 UDP-glucose 
• 108-98-5 thiophenol 
• 83-87-4 D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide 
• 60619-58-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide 
• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 13992-16-0 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 71676-30-7 (4aR,6R,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 150935-64-1 phenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside 
• 152488-26-1 phenyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 236115-71-2 6-(4-methylbenzenesulfonate)-phenyl-1-thio-β-D-glucopyranoside 
• 498-07-7 levoglucosan 
• 213998-04-0 phenyl 3,6-di-O-pivaloyl-1-thio-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 
• 225241-34-9 phenyl 4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside 
• 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 
• 136882-37-6 phenyl 6-O-benzyl-1-thio-β-D-glucopyranoside 
• 273749-60-3 phenyl 4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside 
• 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 
• 263543-42-6 phenyl 3,4-O-(2’,3’-dimethoxybutane-2’,3’-diyl)-1-thio-α-D-mannopyranoside 
• 262605-68-5 phenyl 6-O-triphenylmethyl-1-thio-α-D-mannopyranoside 

Relevant articles and documents

Superarming of glycosyl donors by combined neighboring and conformational effects

A novel glycosyl donor that combines the concepts of both conformational and electronic superarming has been synthesized. The reactivity and selectivity of the donor have been tested in competition experiments.

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.

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.