One-pot synthesis of (±)-1′a-carba-1′aβ-hydroxycytidine - a new carbocyclic analogue of cytidine

Dhimant H. Desai; Azzouz Ben Cheikh; Jiri Zemlicka

doi:10.1016/0040-4039(91)80147-X

One-pot synthesis of (±)-1′a-carba-1′aβ-hydroxycytidine - a new carbocyclic analogue of cytidine

Dhimant H. Desai, Azzouz Ben Cheikh, Jiri Zemlicka

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Abstract

The title compound 1 was synthesized by a one-pot (two-step) procedure starting from aminocyclopentane tetrol 2 and BrCN at pH 9 followed by reaction with cyanoacetylene in 1 M NH₄OH. Oxazolines 3 and 4 are intermediates in the synthesis.

Original language	English (US)
Pages (from-to)	6281-6284
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	44
DOIs	https://doi.org/10.1016/0040-4039(91)80147-X
State	Published - Oct 28 1991

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "One-pot synthesis of (±)-1′a-carba-1′aβ-hydroxycytidine - a new carbocyclic analogue of cytidine",

abstract = "The title compound 1 was synthesized by a one-pot (two-step) procedure starting from aminocyclopentane tetrol 2 and BrCN at pH 9 followed by reaction with cyanoacetylene in 1 M NH4OH. Oxazolines 3 and 4 are intermediates in the synthesis.",

author = "Desai, {Dhimant H.} and Cheikh, {Azzouz Ben} and Jiri Zemlicka",

note = "Funding Information: was supported in part by grant CA32779 from the National Cancer Institute and in part by an institutional grant from the United Way of Southeastern Michigan to the Michigan Cancer Foundation.",

year = "1991",

month = oct,

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doi = "10.1016/0040-4039(91)80147-X",

language = "English (US)",

volume = "32",

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journal = "Tetrahedron Letters",

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publisher = "Elsevier Limited",

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T1 - One-pot synthesis of (±)-1′a-carba-1′aβ-hydroxycytidine - a new carbocyclic analogue of cytidine

AU - Desai, Dhimant H.

AU - Cheikh, Azzouz Ben

AU - Zemlicka, Jiri

N1 - Funding Information: was supported in part by grant CA32779 from the National Cancer Institute and in part by an institutional grant from the United Way of Southeastern Michigan to the Michigan Cancer Foundation.

PY - 1991/10/28

Y1 - 1991/10/28

N2 - The title compound 1 was synthesized by a one-pot (two-step) procedure starting from aminocyclopentane tetrol 2 and BrCN at pH 9 followed by reaction with cyanoacetylene in 1 M NH4OH. Oxazolines 3 and 4 are intermediates in the synthesis.

AB - The title compound 1 was synthesized by a one-pot (two-step) procedure starting from aminocyclopentane tetrol 2 and BrCN at pH 9 followed by reaction with cyanoacetylene in 1 M NH4OH. Oxazolines 3 and 4 are intermediates in the synthesis.

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U2 - 10.1016/0040-4039(91)80147-X

DO - 10.1016/0040-4039(91)80147-X

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

One-pot synthesis of (±)-1′a-carba-1′aβ-hydroxycytidine - a new carbocyclic analogue of cytidine

Abstract

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