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

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 [...

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Published inTetrahedron Vol. 51; no. 23; pp. 6419 - 6430
Main Authors Itaya, Taisuke, Watanabe, Nobuhide, Iida, Takehiko, Kanai, Tae, Mizutani, Akemi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 05.06.1995
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TRANSFER RNA-PHE
PALLADIUM
ABSOLUTE-CONFIGURATION
ALLYLIC CARBONATES
HYDROXY-Y BASE
DEOXYGENATION
OXALYL CHLORIDE
NEUTRAL CONDITIONS
CYCLIC CARBONATES
FLUORESCENT MINOR BASE
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Summary: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. The first synthesis of β-hydroxywybutines has been achieved by oxidation of the methyl butenoate, followed by deoxygenation via the cyclic carbonates.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(95)00302-O