Controlled Synthesis of Enantio-, Regio-, and Diastereomers of Amino-4-pentenediols from 1,4-Pentadien-3-ol via Epoxy-4-pentenols I.erythro-1-Amino-4-pentene-2,3-diols
- 1 January 1991
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1991 (09) , 769-776
- https://doi.org/10.1055/s-1991-26571
Abstract
erythro-1-Amino-4-pentene-2,3-diols 7, 8 of both the L- and D-series are readily accessible in high purity from 1,4-pentadien-3-ol via the 1,2-epoxy-4-pentenols 2, 4 by treatment with ammonia, primary aliphatic or aromatic amines, secondary aliphatic or a heterocyclic amine (imidazole, 6j). 9-(2,3-Dihydroxy-4-penten-1-yl)adenines of the erythro-L- and -D-form 7k, 8k are obtained from 2 (L-erythro) via 1-chloro-4-pentene-2,3-diol (9) and from D-ribonolactone via the 1-mesyloxy-4-pentene-2,3-diol (12) (D-erythro), respectively.Keywords
This publication has 0 references indexed in Scilit: