REACTIONS OF SUGAR CHLOROSULFATES: VII. SOME CONFORMATIONAL ASPECTS

• Published in: Canadian journal of chemistry Vol. 44; no. 13; pp. 1483 - 1491
• Main Authors: Cottrell, A. G, Buncel, E, Jones, J. K. N
• Format: Journal Article
• Language: English
• Published: Ottawa, Canada NRC Research Press 01.07.1966
• ISSN: 0008-4042; 1480-3291
• DOI: 10.1139/v66-223

The reaction of sulfuryl chloride with several 1,6-anhydro-hexosans has yielded crystalline, fully chlorosulfated derivatives. Replacement of the chlorosulfate moieties by chlorodeoxy groups could not be achieved under the reaction conditions employed. This non-reactivity is discussed in terms of steric interactions in the transition state for substitution.An examination of some chloro-substituted sugar chlorosulfates confirmed that an axial chlorodeoxy group in a glycopyranoside deactivates a neighboring equatorial chlorosulfate group and thus prevents further chlorodeoxy groups being introduced into such positions. Methyl α- D -altropyranoside, methyl α- L -rhamnopyranoside, methyl α- D -lyxopyranoside, L -rhamnose, and D -lyxose were reacted with sulfuryl chloride. The resulting products were those expected if these sugars reacted primarily in the C1 conformation.