Synthesis of pyridine-stretched 2′-deoxynucleosides

Russell Clayton; Michael L. Davis; William Fraser; Wei Li; Christopher A. Ramsden

doi:10.1055/s-2002-33505

Synthesis of pyridine-stretched 2′-deoxynucleosides

Russell Clayton
, Michael L. Davis
, William Fraser
, Wei Li
, Christopher A. Ramsden

Keele University
Aston University

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

Synthesis of novel pyridine-stretched nucleoside (PSN) analogues of adenine (strA) (1), 2,6-diaminopurine (strD) (15) and hypoxanthine (strH) (17) from 4(5)-nitroimidazole has been achieved. Glycosylation of 4(5)-nitroimidazole was optimized to give consistently good yields (>70%) of the desired analytically pure 5-nitro-1′-β isomer 8 which on hydrogenation, C-addition of ethoxymethylene malononitrile (EMMN) and cyclisation provides the key intermediate 14 for PSN synthesis.

Original language	English
Pages (from-to)	1483-1486
Number of pages	4
Journal	Synlett
Issue number	9
Early online date	17 Sept 2002
DOIs	https://doi.org/10.1055/s-2002-33505
Publication status	Published - 2002

Keywords

2′-deoxynucleosides
5-aminoimidazoles
DNA - lin-pyridoadenosine
glycosylation
nucleoside analogues

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10.1055/s-2002-33505

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title = "Synthesis of pyridine-stretched 2′-deoxynucleosides",

abstract = "Synthesis of novel pyridine-stretched nucleoside (PSN) analogues of adenine (strA) (1), 2,6-diaminopurine (strD) (15) and hypoxanthine (strH) (17) from 4(5)-nitroimidazole has been achieved. Glycosylation of 4(5)-nitroimidazole was optimized to give consistently good yields (>70\%) of the desired analytically pure 5-nitro-1′-β isomer 8 which on hydrogenation, C-addition of ethoxymethylene malononitrile (EMMN) and cyclisation provides the key intermediate 14 for PSN synthesis.",

keywords = "2′-deoxynucleosides , 5-aminoimidazoles , DNA - lin-pyridoadenosine , glycosylation , nucleoside analogues",

author = "Russell Clayton and Davis, \{Michael L.\} and William Fraser and Wei Li and Ramsden, \{Christopher A.\}",

year = "2002",

doi = "10.1055/s-2002-33505",

language = "English",

pages = "1483--1486",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "9",

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T1 - Synthesis of pyridine-stretched 2′-deoxynucleosides

AU - Clayton, Russell

AU - Davis, Michael L.

AU - Fraser, William

AU - Li, Wei

AU - Ramsden, Christopher A.

PY - 2002

Y1 - 2002

N2 - Synthesis of novel pyridine-stretched nucleoside (PSN) analogues of adenine (strA) (1), 2,6-diaminopurine (strD) (15) and hypoxanthine (strH) (17) from 4(5)-nitroimidazole has been achieved. Glycosylation of 4(5)-nitroimidazole was optimized to give consistently good yields (>70%) of the desired analytically pure 5-nitro-1′-β isomer 8 which on hydrogenation, C-addition of ethoxymethylene malononitrile (EMMN) and cyclisation provides the key intermediate 14 for PSN synthesis.

AB - Synthesis of novel pyridine-stretched nucleoside (PSN) analogues of adenine (strA) (1), 2,6-diaminopurine (strD) (15) and hypoxanthine (strH) (17) from 4(5)-nitroimidazole has been achieved. Glycosylation of 4(5)-nitroimidazole was optimized to give consistently good yields (>70%) of the desired analytically pure 5-nitro-1′-β isomer 8 which on hydrogenation, C-addition of ethoxymethylene malononitrile (EMMN) and cyclisation provides the key intermediate 14 for PSN synthesis.

KW - 2′-deoxynucleosides

KW - 5-aminoimidazoles

KW - DNA - lin-pyridoadenosine

KW - glycosylation

KW - nucleoside analogues

UR - https://www.scopus.com/pages/publications/0036375549

UR - https://www.thieme-connect.de/DOI/DOI?10.1055/s-2002-33505

U2 - 10.1055/s-2002-33505

DO - 10.1055/s-2002-33505

M3 - Article

AN - SCOPUS:0036375549

SN - 0936-5214

SP - 1483

EP - 1486

JO - Synlett

JF - Synlett

IS - 9

ER -

Synthesis of pyridine-stretched 2′-deoxynucleosides

Abstract

Keywords

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