Synthesis of [R-(R,S)]- and [S-(R,R)]β-, the most probable alternatives for the hypermodified nucleoside of rat liver phenylalanine transfer ribonucleic acid

Autor:	Taisuke Itaya, Takehiko Iida, Tae Kanai
Rok vydání:	1997
Předmět:	Triphosgene Stereochemistry Organic Chemistry Diastereomer Phenylalanine Biochemistry Catalysis chemistry.chemical_compound chemistry Hydrogenolysis Drug Discovery Wittig reaction Trimethylsilyldiazomethane Nucleoside
Zdroj:	Tetrahedron Letters. 38:1979-1982
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(97)00253-0
Popis:	The synthesis of the title compounds started with the Vilsmeier reaction of 3-[2,3,5- tris -O-(tert- butyldimethylsilyl)-β- d - ribofuranosyl]wye ( 5b ) and proceeded through the Wittig reaction with ( R )- N -(methoxycarbonyl)-3-(triphenylphosphonio)alaninate ( 4 ), methylation with trimethylsilyldiazomethane, OsO 4 oxidation, cyclocondensation with triphosgene, and catalytic hydrogenolysis. Chromatographic separation of the resulting diastereomeric mixture and subsequent deprotection afforded the two desired nucleoside [ [R-(R ∗ ,S ∗ )]- and [S-(R ∗ ,R ∗ )]- 2b ] for the first time.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::96c1e6f2fad4ab259206caa3164b1c25 https://doi.org/10.1016/s0040-4039(97)00253-0 Zobrazit plný text záznamu Full Text from ScienceDirect