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Synthesis of β-hydroxywybutines, the most probable alternatives for the hypermodified base of rat liver phenylalanine transfer ribonucleic acid

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
51
Issue
23
Identifiers
DOI: 10.1016/0040-4020(95)00302-o

Abstract

Abstract Deoxygenation of the 1,2-glycol (±)- 5 was achieved at the position adjacent to the heterocycle through the cyclic carbonate (±)- 14, providing the monohydroxy compound 6. This new method of regioselective deoxygenation was employed for the first synthesis of β-hydroxywybutines [[R-(R ∗,S ∗)]- and [S-(R ∗,R ∗)]-2] : oxidation of the methyl butenoate 7 with osmium tetroxide, followed by deoxygenation through the cyclic carbonates ( 19 and 20), afforded the two diastereomers of 2.

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