82919-97-9

Basic information

• Product Name: 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-galactopyranosyl 3-O-acetyl-1,4,6-trichloro-1,4,6-trideoxy-β-D-sorbofuranoside
• Synonyms: 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-galactopyranosyl 3-O-acetyl-1,4,6-trichloro-1,4,6-trideoxy-β-D-sorbofuranoside
• CAS NO: 82919-97-9
• Molecular Weight: 584.232
• Mol File: 82919-97-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-galactopyranosyl 3-O-acetyl-1,4,6-trichloro-1,4,6-trideoxy-β-D-sorbofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-galactopyranosyl 3-O-acetyl-1,4,6-trichloro-1,4,6-trideoxy-β-D-sorbofuranoside(82919-97-9)
• EPA Substance Registry System: 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-galactopyranosyl 3-O-acetyl-1,4,6-trichloro-1,4,6-trideoxy-β-D-sorbofuranoside(82919-97-9)

Safety Data

• Hazardous Substances Data: 82919-97-9(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 63648-81-7 6-O-acetyl sucrose 

Relevant articles and documents

SYNTHESIS OF AN INTENSELY SWEET CHLORODEOXYSUCROSE: MECHANISM OF 4'-CHLORINATION OF SUCROSE BY SULPHURYL CHLORIDE

Reaction of 6-acetylsucrose with sulphuryl chloride in chloroform-pyridine affords, after dechlorosulphation and acetylation, a mixture of two isomeric 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-galactopyranosyl 3-O-acetyl-1,4,6,-trichloro-1,4,6-trideoxy-β-D-hexulofuranosides (6 and 7) and 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-galactopyranosyl 3,4-di-O-acetyl-1,6-dichloro-1,6-dideoxy-β-D-fructofuranoside (4).Chlorination of C-4, C-1', and C-6' occurs by direct displacement of the initially formed chlorosulphonyloxy groups by chloride ions, but displacement of the 4'-chlorosulphate is sterically hindered.The introdution of a 4'-chloro substituent involves ring opening of intermediate 3',4'-epoxides by chloride ions, the ribo-epoxide producing the sorbo-isomer 6 and the lyxo-epoxide giving the fructo-isomer 7.The proposed mechanism is supported by the formation of 4-chloro-4-deoxyfructofuranosides when 3',4'-lyxo-hexulofuranosides are treated with sulphuryl chloride under the same conditions.