Erythrose sesqui-acetals as electrophiles. 2-Deoxy-C-nucleosides from D-glucose.

Robin Polt; Thusitha Wijayarathe

doi:10.1016/S0040-4039(00)93472-5

Erythrose sesqui-acetals as electrophiles. 2-Deoxy-C-nucleosides from D-glucose.

Robin Polt
, Thusitha Wijayarathe

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

13 Scopus citations

Abstract

Cleavage of glucosides with NalO₄ in MeOH furnishes sesqui-acetals (protected dialdehydes). Olefination of these substrates, followed by endocyclic oxymercuration-demercuration furnishes substituted tetrahydrofurans (1,2-dideoxy-1-aryl-D-ribofuranoses). Proper choice of protecting groups can affect the face selectivity of the oxymercuration step to provide only the desired β-C-anomer.

Original language	English (US)
Pages (from-to)	4831-4834
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	37
DOIs	https://doi.org/10.1016/S0040-4039(00)93472-5
State	Published - Sep 9 1991

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Erythrose sesqui-acetals as electrophiles. 2-Deoxy-C-nucleosides from D-glucose.",

abstract = "Cleavage of glucosides with NalO4 in MeOH furnishes sesqui-acetals (protected dialdehydes). Olefination of these substrates, followed by endocyclic oxymercuration-demercuration furnishes substituted tetrahydrofurans (1,2-dideoxy-1-aryl-D-ribofuranoses). Proper choice of protecting groups can affect the face selectivity of the oxymercuration step to provide only the desired β-C-anomer.",

author = "Robin Polt and Thusitha Wijayarathe",

note = "Funding Information: It is noteworthy that the synthetic approach described in this paper is short and highly convergent. Work is presently underway to extend this methodology to more biologically relevant targets by using heterocyclic Wittig reagents.It, ls Acknowledgement. We would like to thank Dr. Jaroslav Zajicek for his assistance with the NMR, and the Department of Chemistry at the University of Arizona for the financial support of this work.",

year = "1991",

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doi = "10.1016/S0040-4039(00)93472-5",

language = "English (US)",

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journal = "Tetrahedron Letters",

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T1 - Erythrose sesqui-acetals as electrophiles. 2-Deoxy-C-nucleosides from D-glucose.

AU - Polt, Robin

AU - Wijayarathe, Thusitha

N1 - Funding Information: It is noteworthy that the synthetic approach described in this paper is short and highly convergent. Work is presently underway to extend this methodology to more biologically relevant targets by using heterocyclic Wittig reagents.It, ls Acknowledgement. We would like to thank Dr. Jaroslav Zajicek for his assistance with the NMR, and the Department of Chemistry at the University of Arizona for the financial support of this work.

PY - 1991/9/9

Y1 - 1991/9/9

N2 - Cleavage of glucosides with NalO4 in MeOH furnishes sesqui-acetals (protected dialdehydes). Olefination of these substrates, followed by endocyclic oxymercuration-demercuration furnishes substituted tetrahydrofurans (1,2-dideoxy-1-aryl-D-ribofuranoses). Proper choice of protecting groups can affect the face selectivity of the oxymercuration step to provide only the desired β-C-anomer.

AB - Cleavage of glucosides with NalO4 in MeOH furnishes sesqui-acetals (protected dialdehydes). Olefination of these substrates, followed by endocyclic oxymercuration-demercuration furnishes substituted tetrahydrofurans (1,2-dideoxy-1-aryl-D-ribofuranoses). Proper choice of protecting groups can affect the face selectivity of the oxymercuration step to provide only the desired β-C-anomer.

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UR - https://www.scopus.com/pages/publications/0025741851#tab=citedBy

U2 - 10.1016/S0040-4039(00)93472-5

DO - 10.1016/S0040-4039(00)93472-5

M3 - Article

AN - SCOPUS:0025741851

SN - 0040-4039

VL - 32

SP - 4831

EP - 4834

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Erythrose sesqui-acetals as electrophiles. 2-Deoxy-C-nucleosides from D-glucose.

Abstract

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