Regiospecific Dehydration of Some Branched Cycloses and Cyclitols Derived From Activated 2,6-Heptodiulose Derivatives
- 1 January 1983
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 2 (2) , 201-205
- https://doi.org/10.1080/07328308308057868
Abstract
The stereoselective base catalyzed conversion of tri-0-acetyl-l,7-dichloro-l,7-dideoxy-xylo-2,6-heptodiulose to d l-(2,3,4,6/5)-4,5,6-tri-0-acetyl-2-chloro-3-C-(chloromethyl)-3,4,5,6-tetrahydroxy-cyclohexanone has been described,1 and it has also been shown that branched cyclose formation from the corresponding 1,7-dibromo and 1,7-diazido-2,6-heptodiuloses also occurs in the same stereoselective manner.1 Reduction of the cyclose ketone function followed by appropriate deprotective leads to branched epi-inositols.1,2 The general structure of the starting 2,6-heptodiulose, and the product cyclose and cyclitol are given as I, II and III respectively.Keywords
This publication has 4 references indexed in Scilit:
- A New Synthesis of Branched-Chain Epi-Configuration Deoxyhalogeno- and DeoxyaminocyclitolsPublished by American Chemical Society (ACS) ,1980
- Branched-chain halo- and animo-cyclitols: synthesis and an x-ray crystallographic studyCarbohydrate Research, 1980
- The unsaturated cyclitol part of the new antibiotics, the validamycinsJournal of the Chemical Society, Chemical Communications, 1972
- Steroidal Cyclic Ketals. XII.1 The Preparation of Δ16-SteroidsJournal of the American Chemical Society, 1955