Stereoselective synthesis of deoxycarbaheptopyranose derivatives: 5a-carba-6-deoxy-alpha-DL-galacto-heptopyranose and 5a-carba-6-deoxy-alpha-DL-gulo-heptopyranose

Date

2011-02-11

Author

Kishali, Nurhan Horasan
Dogan, Dilem
ŞAHİN, Ertan
GÜNEL, ASLIHAN
KARA, Yunus
Balcı, Metin

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Two new deoxycarbaheptopyranoses, 5a-carba-6-deoxy-alpha-DL-galacto-heptopyranose and 5a-carba-6-deoxy-alpha-DL-gulo-heptopyranose were prepared starting from cyclohexa-1,4-diene. The addition of dichloroketene to cyclohexa-1,4-diene followed by the subsequent reductive elimination and Baeyer-Villiger oxidation in turn led to the formation of a bicyclic lactone. Reduction of the lactone moiety followed by acetylation gave a diacetate with cis-configuration. The introduction of additional acetate functionality into the molecule was achieved by singlet oxygen ene-reaction. The formed hydroperoxide was reduced and then acetylated. The triacetate was further functionalized either by direct cis-hydroxylation using OsO4 or by epoxidation followed by a ring-opening reaction to give the title heptopyranose derivatives. One of the synthesized molecules, galacto-heptopyranose exhibited enzyme specific inhibition against alpha-glycosidase. On the other hand, they did not show any inhibition for alpha-amylase. However, both compounds, gulo-heptopyranose and galacto-heptopyranose increased the activity of alpha-amylase.

Subject Keywords

Carbapyranose, Deoxycarbasugar, Carbasugar, Heptopyranose, Inositol, Cyclitol

URI

https://hdl.handle.net/11511/56924

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2010.11.102

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Graduate School of Natural and Applied Sciences, Article

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Citation Formats

N. H. Kishali, D. Dogan, E. ŞAHİN, A. GÜNEL, Y. KARA, and M. Balcı, “Stereoselective synthesis of deoxycarbaheptopyranose derivatives: 5a-carba-6-deoxy-alpha-DL-galacto-heptopyranose and 5a-carba-6-deoxy-alpha-DL-gulo-heptopyranose,” TETRAHEDRON, pp. 1193–1200, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56924.