74774-11-1

Basic information

• Product Name: .beta.-D-Glucopyranose, 1,6-anhydro-6-C-(phenylthio)-, triacetate, (6R)-
• Synonyms: .beta.-D-Glucopyranose, 1,6-anhydro-6-C-(phenylthio)-, triacetate, (6R)-
• CAS NO: 74774-11-1
• Molecular Formula: C₁₈H₂₀O₈S
• Molecular Weight: 0
• Mol File: 74774-11-1.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: .beta.-D-Glucopyranose, 1,6-anhydro-6-C-(phenylthio)-, triacetate, (6R)-(CAS DataBase Reference)
• NIST Chemistry Reference: .beta.-D-Glucopyranose, 1,6-anhydro-6-C-(phenylthio)-, triacetate, (6R)-(74774-11-1)
• EPA Substance Registry System: .beta.-D-Glucopyranose, 1,6-anhydro-6-C-(phenylthio)-, triacetate, (6R)-(74774-11-1)

Safety Data

• Hazardous Substances Data: 74774-11-1(Hazardous Substances Data)

Upstream product

• 13242-55-2 2,3,4-tri-O-acetyllevoglucosan 
• 3111-52-2 potassium thiophenolate 
• 74774-10-0 (6S)-2,3,4,-tri-O-acetyl-1,6-anhydro-6-bromo-β-D-glucopyranose 

Downstream Products

• 98853-88-4 (1R,2S,3S,4R,5R,7S)-2,3,4-Tris-benzyloxy-7-ethyl-6,8-dioxa-bicyclo[3.2.1]octane 
• 88111-83-5 (1R,5S)-6-exo,7-endo,8-exo-triacetoxy-N-methyl-4-endo-phenylthio-3-oxa-2-azabicyclo<3.3.0>octane 
• 88196-01-4 (1R,5S)-6-exo,7-endo,8-exo-triacetoxy-N-methyl-4-exo-phenylthio-3-oxa-2-azabicyclo<3.3.0>octane 
• 88111-89-1 (1R,5S)-4-endo,6-exo,7-endo,8-exo-tetra-acetoxy-N-methyl-3-oxa-2-azabicyclo<3.3.0>octane 
• 88111-89-1 (1R,5S)-4-exo,6-exo,7-endo,8-exo-tetra-acetoxy-N-methyl-3-oxa-2-azabicyclo<3.3.0>octane 
• 88111-85-7 (6S)-3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-6-phenylthio-D-arabino-hex-1-enitol 
• 88111-85-7 (6R)-3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-6-phenylthio-D-arabino-hex-1-enitol 
• 88111-93-7 E-(3S,4S,5R)-3,4-diacetoxy-5-(N-hydroxy-N-methylamino)-1-<2-(phenylthio)vinyl>cyclopent-1-ene 
• 88111-93-7 Z-(3S,4S,5R)-3,4-diacetoxy-5-(N-hydroxy-N-methylamino)-1-<2-(phenylthio)vinyl>cyclopent-1-ene 
• 88111-88-0 (1R,5S)-6-exo,7-endo,8-exo-triacetoxy-4-exo-hydroxy-N-methyl-3-oxa-2-azabicyclo<3.3.0>octane 
• 88111-84-6 3,4-di-O-acetyl-1,5-anhydro-2-deoxy-6-S-phenyl-6-thio-D-arabino-hex-1-enitol 
• 88111-82-4 (6S)-2,3,4-tri-O-acetyl-1,6-anhydro-6-phenylthio-β-D-glucopyranose 
• 74774-20-2 (6RS)-2,3,4,6-tetra-O-acetyl-6-phenylthio-β-D-glucopyranosyl acetate 
• 88111-81-3 (6RS)-2,3,4-tri-O-acetyl-6-bromo-6-S-phenyl-6-thio-α-D-glucopyranosyl bromide 

Relevant articles and documents

Photobromination of Carbohydrate Derivatives. VI. Funcionalization at C6 of 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-glucopyranose

Photobromination of 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-glucopyranose gives the syrupy 6S (exo) bromide in high yield; further reaction leads to secondary bromination at this position.The monobromide reacts with methanol and thiophenol under conditions of kinetic control to give mainly the endo-methoxy and phenylthio derivatives formed by direct nucleophilic displacement, and from the latter the exo-methoxy acetal was obtained by a second nucleophilic substitution.Acetolysis of these compounds can lead to the coresponding exo-6-acetoxy ester or monocyclicproducts formed by opening of the five-membered rings.