82950-42-3

Upstream product

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

Relevant academic research and scientific papers

Synthesis, structure and sweetness of 4-chloro-4-deoxy-α-d-galactopyranosyl 1,4,6-trichloro-1,4,6-trideoxy-β-d-tagatofuranoside

The reaction of 6-O-acetylsucrose with sulfuryl chloride was reexamined. The major product, after dechlorosulfation and acetylation, was determined by X-ray diffraction to be 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-tagatofuranoside and not the corresponding sorbofuranoside, as reported earlier. The mechanism of chlorination at C-4′ is discussed. The intensity of sweetness of the free 4′-chlorodeoxy tagato isomer is determined to be only about one-tenth the sweetness of the corresponding chlorodeoxy fructo isomer, which strongly suggests that the hydrophobic γ-site is located at C-4′.

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.