Synthesis and structure of 2-pyransoylperimidines

Iain A. S. Smellie; Andreas Fromm; Stephen A. Moggach; R. Michael Paton

doi:10.1016/j.carres.2010.09.028

Synthesis and structure of 2-pyransoylperimidines

Iain A. S. Smellie, Andreas Fromm, Stephen A. Moggach, R. Michael Paton

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Abstract

The first examples of 2-pyranosylperimidines are reported. The beta-D-glucopyranosyl nitrile oxide 5, generated by base-induced dehydrochlorination of the hydroximoyl chloride 4, reacted with 1,8-diaminonaphthalene to afford the 2-(beta-D-glucopyranosyl)perimidine 8. The D-xylo-, D-galacto-, D-manno- and D-glycero analogues 12, 15, 16 and 19 were prepared similarly. The glycals 9 and 13 were formed as by-products resulting from elimination of acetic acid from the corresponding pyranosylperimidines. The structure of D-glucose-derived perimidine 8 was established by X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	43-49
Number of pages	7
Journal	Carbohydrate Research
Volume	346
Issue number	1
DOIs	https://doi.org/10.1016/j.carres.2010.09.028
Publication status	Published - 3 Jan 2011
Externally published	Yes

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10.1016/j.carres.2010.09.028

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@article{df4decca9df64033ab7c5257cf85ecf3,

title = "Synthesis and structure of 2-pyransoylperimidines",

abstract = "The first examples of 2-pyranosylperimidines are reported. The beta-D-glucopyranosyl nitrile oxide 5, generated by base-induced dehydrochlorination of the hydroximoyl chloride 4, reacted with 1,8-diaminonaphthalene to afford the 2-(beta-D-glucopyranosyl)perimidine 8. The D-xylo-, D-galacto-, D-manno- and D-glycero analogues 12, 15, 16 and 19 were prepared similarly. The glycals 9 and 13 were formed as by-products resulting from elimination of acetic acid from the corresponding pyranosylperimidines. The structure of D-glucose-derived perimidine 8 was established by X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.",

keywords = "Perimidines, Nitrile oxides, C-Glycosides, X-ray crystallography, GLYCOGEN-PHOSPHORYLASE INHIBITORS, PYRANOSYL NITRILE OXIDES, X-RAY STRUCTURE, 2-SUBSTITUTED PERIMIDINES, CYCLOADDITION REACTIONS, PERI-ANNELATION, DERIVATIVES, CRYSTAL, BENZIMIDAZOLES, 1,3-DIAZAPYRENES",

author = "Smellie, {Iain A. S.} and Andreas Fromm and Moggach, {Stephen A.} and Paton, {R. Michael}",

year = "2011",

month = jan,

day = "3",

doi = "10.1016/j.carres.2010.09.028",

language = "English",

volume = "346",

pages = "43--49",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier",

number = "1",

}

TY - JOUR

T1 - Synthesis and structure of 2-pyransoylperimidines

AU - Smellie, Iain A. S.

AU - Fromm, Andreas

AU - Moggach, Stephen A.

AU - Paton, R. Michael

PY - 2011/1/3

Y1 - 2011/1/3

N2 - The first examples of 2-pyranosylperimidines are reported. The beta-D-glucopyranosyl nitrile oxide 5, generated by base-induced dehydrochlorination of the hydroximoyl chloride 4, reacted with 1,8-diaminonaphthalene to afford the 2-(beta-D-glucopyranosyl)perimidine 8. The D-xylo-, D-galacto-, D-manno- and D-glycero analogues 12, 15, 16 and 19 were prepared similarly. The glycals 9 and 13 were formed as by-products resulting from elimination of acetic acid from the corresponding pyranosylperimidines. The structure of D-glucose-derived perimidine 8 was established by X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.

AB - The first examples of 2-pyranosylperimidines are reported. The beta-D-glucopyranosyl nitrile oxide 5, generated by base-induced dehydrochlorination of the hydroximoyl chloride 4, reacted with 1,8-diaminonaphthalene to afford the 2-(beta-D-glucopyranosyl)perimidine 8. The D-xylo-, D-galacto-, D-manno- and D-glycero analogues 12, 15, 16 and 19 were prepared similarly. The glycals 9 and 13 were formed as by-products resulting from elimination of acetic acid from the corresponding pyranosylperimidines. The structure of D-glucose-derived perimidine 8 was established by X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.

KW - Perimidines

KW - Nitrile oxides

KW - C-Glycosides

KW - X-ray crystallography

KW - GLYCOGEN-PHOSPHORYLASE INHIBITORS

KW - PYRANOSYL NITRILE OXIDES

KW - X-RAY STRUCTURE

KW - 2-SUBSTITUTED PERIMIDINES

KW - CYCLOADDITION REACTIONS

KW - PERI-ANNELATION

KW - DERIVATIVES

KW - CRYSTAL

KW - BENZIMIDAZOLES

KW - 1,3-DIAZAPYRENES

U2 - 10.1016/j.carres.2010.09.028

DO - 10.1016/j.carres.2010.09.028

M3 - Article

VL - 346

SP - 43

EP - 49

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

IS - 1

ER -