Stereoselective synthesis of deoxycarbaheptopyranose derivatives: 5a-carba-6-deoxy-alpha-DL-galacto-heptopyranose and 5a-carba-6-deoxy-alpha-DL-gulo-heptopyranose
Özet
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. (C) 2010 Elsevier Ltd. All rights reserved.
Anahtar kelimeler
Atıf için künye
Horasan, N., Dogan, D., Şahin, E., Gunel, A., Kara, Y., & Balci, M. (2011). Stereoselective synthesis of deoxycarbaheptopyranose derivatives: 5a-carba-6-deoxy-alpha-DL-galacto-heptopyranose and 5a-carba-6-deoxy-alpha-DL-gulo-heptopyranose. TETRAHEDRON, 67(6), 1193–1200. https://doi.org/10.1016/j.tet.2010.11.102
BibTeX
@article{horasan2011-66689,
author = {Horasan, Nurhan and Dogan, Dilem and Şahin, Ertan and Gunel, Aslihan and Kara, Yunus and Balci, Metin},
title = {Stereoselective synthesis of deoxycarbaheptopyranose derivatives: 5a-carba-6-deoxy-alpha-DL-galacto-heptopyranose and 5a-carba-6-deoxy-alpha-DL-gulo-heptopyranose},
journal = {TETRAHEDRON},
year = {2011},
volume = {67},
number = {6},
pages = {1193--1200},
issn = {0040-4020},
doi = {10.1016/j.tet.2010.11.102},
url = {https://akademik.atauni.edu.tr/yayinlar/66689-stereoselective-synthesis-of-deoxycarbaheptopyranose-derivatives-5a-carba-6}
}