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D-glucosamine trimethylene dithioacetal derivatives: formation of six- and seven-membered ring amino carbasugars. Synthesis of (-)-calystegine B3.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2007 Oct 21; Vol. 5 (20), pp. 3330-9. Date of Electronic Publication: 2007 Sep 06. - Publication Year :
- 2007
-
Abstract
- By virtue of carefully chosen protecting groups, d-glucosamine trimethylene dithioacetal derivatives were successfully oxidized to the corresponding 6-aldehydes. This methodology reverses the donor and acceptor position on a normal open chain sugar and changes the relative position of the N-substituent. From the 6-aldehydes, heptose epoxide derivatives were prepared by a Corey-Chaykovsky reaction, and cyclized by the Corey-Seebach method. Depending on the designed protecting groups, the orthogonally protected six- and seven-membered ring amino carbasugars can be produced selectively and efficiently. (-)-Calystegine B(3) was synthesized from one of those products with high yield. This is the first anionic cyclization pathway to calystegine type structures.
Details
- Language :
- English
- ISSN :
- 1477-0520
- Volume :
- 5
- Issue :
- 20
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 17912387
- Full Text :
- https://doi.org/10.1039/b711112f