Synthetic route to 5-substituted uridines via a new type of desulfurizative stannylation
Identifieur interne : 000324 ( Istex/Corpus ); précédent : 000323; suivant : 000325Synthetic route to 5-substituted uridines via a new type of desulfurizative stannylation
Auteurs : Hiromichi Tanaka ; Hiroyuki Hayakawa ; Kikoh Obi ; Miyasaka TadashiSource :
- Tetrahedron [ 0040-4020 ] ; 1986.
English descriptors
- KwdEn :
- Anal, Benzene, Calcd, Cdcl, Chcl, Chem, Column chromatography, Derivative, Desulfurizative, Desulfurizative stannylation, Deuteration, Equiv, Etoh, Hayakawa, Ltmp, Meoh, Miyasaka, Mmol, Phenylthio group, Physical data, Reagent, Room temperature, Silica, Stannylation, Tanaka, Tbth, Tetrahedron, Tetrahedron lett.
- Teeft :
- Anal, Benzene, Calcd, Cdcl, Chcl, Chem, Column chromatography, Derivative, Desulfurizative, Desulfurizative stannylation, Deuteration, Equiv, Etoh, Hayakawa, Ltmp, Meoh, Miyasaka, Mmol, Phenylthio group, Physical data, Reagent, Room temperature, Silica, Stannylation, Tanaka, Tbth, Tetrahedron, Tetrahedron lett.
Abstract
Abstract: phenylthio group at the C-6 position of uridine serves as the protecting group during lithiation at the C-5 position with lithium 2,2,6,6-tetramethylpiperidide. Reactions of the resulting C-5 lithiated species with various types of electrophiles furnish 5-substituted 6-phenylthiouridine derivatives. The phenylthio group in these products can be removed by a new type of desulfurizative stannylation with tributyltin hydride followed by protonolysis. The whole sequence constitutes a new route to 5-substituted uridines. Application of this method to 2'-deoxyuridine is also described.
Url:
DOI: 10.1016/S0040-4020(01)87642-0
Links to Exploration step
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<front><div type="abstract" xml:lang="en">Abstract: phenylthio group at the C-6 position of uridine serves as the protecting group during lithiation at the C-5 position with lithium 2,2,6,6-tetramethylpiperidide. Reactions of the resulting C-5 lithiated species with various types of electrophiles furnish 5-substituted 6-phenylthiouridine derivatives. The phenylthio group in these products can be removed by a new type of desulfurizative stannylation with tributyltin hydride followed by protonolysis. The whole sequence constitutes a new route to 5-substituted uridines. Application of this method to 2'-deoxyuridine is also described.</div>
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<ce:abstract-sec><ce:simple-para>phenylthio group at the C-6 position of uridine serves as the protecting group during lithiation at the C-5 position with lithium 2,2,6,6-tetramethylpiperidide. Reactions of the resulting C-5 lithiated species with various types of electrophiles furnish 5-substituted 6-phenylthiouridine derivatives. The phenylthio group in these products can be removed by a new type of desulfurizative stannylation with tributyltin hydride followed by protonolysis. The whole sequence constitutes a new route to 5-substituted uridines. Application of this method to 2'-deoxyuridine is also described.</ce:simple-para>
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<abstract lang="en">Abstract: phenylthio group at the C-6 position of uridine serves as the protecting group during lithiation at the C-5 position with lithium 2,2,6,6-tetramethylpiperidide. Reactions of the resulting C-5 lithiated species with various types of electrophiles furnish 5-substituted 6-phenylthiouridine derivatives. The phenylthio group in these products can be removed by a new type of desulfurizative stannylation with tributyltin hydride followed by protonolysis. The whole sequence constitutes a new route to 5-substituted uridines. Application of this method to 2'-deoxyuridine is also described.</abstract>
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