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

Article abstract of DOI:10.1080/07328309908543993

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′.

Full text of DOI:10.1080/07328309908543993

Journal of Carbohydrate Chemistry
ISSN: 0732-8303 (Print) 1532-2327 (Online) Journal homepage: http://www.tandfonline.com/loi/lcar20
Synthesis, Structure and Sweetness Of 4-Chloro-4-
Deoxy-α-D-Galactopyranosyl 1,4,6-Trichloro-1,4,6-
Trideoxy-β-D-Tagatofuranoside
C. Kuan Lee , H. Chuan Kang & Anthony Linden
To cite this article: C. Kuan Lee , H. Chuan Kang & Anthony Linden (1999) Synthesis,
Structure and Sweetness Of 4-Chloro-4-Deoxy-α-D-Galactopyranosyl 1,4,6-Trichloro-1,4,6-
Trideoxy-β-D-Tagatofuranoside, Journal of Carbohydrate Chemistry, 18:2, 241-253, DOI:
10.1080/07328309908543993
To link to this article: http://dx.doi.org/10.1080/07328309908543993
Published online: 27 Feb 2008.
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Date: 15 June 2016, At: 22:13