Synthesis of 1-(β-D-glucopyranosyl) pyrimidin-2(1H)-ones from 2-chloropyrimidines

Ibrahim M. Abdou; Lucjan Strekowski; Mohamed F. Abdel-Megeed; Adel M.E. Attia; Mahmoud A. Omara

Synthesis of 1-(β-D-glucopyranosyl) pyrimidin-2(1H)-ones from 2-chloropyrimidines

Ibrahim M. Abdou
, Lucjan Strekowski
, Mohamed F. Abdel-Megeed
, Adel M.E. Attia
, Mahmoud A. Omara

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

Abstract

Tetra-O-acetyl derivatives 10-12 of the title compounds are easily obtained by hydrolysis of 2-chloropyrimidines 1-3 followed by coupling of the resultant pyrimidin-2(1H)-ones 4-6 with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide under basic conditions (method A) or treatment of 1-3 with potassium trimethylsilanolate followed by coupling of the resultant 2-(trimethylsilyloxy)pyrimidines, without isolation, with β-D-glucose pentaacetate in the presence of tin tetrachloride (method B).

Original language	English
Pages (from-to)	295-300
Number of pages	6
Journal	Heterocyclic Communications
Volume	3
Issue number	4
Publication status	Published - 1997
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

Cite this

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title = "Synthesis of 1-(β-D-glucopyranosyl) pyrimidin-2(1H)-ones from 2-chloropyrimidines",

abstract = "Tetra-O-acetyl derivatives 10-12 of the title compounds are easily obtained by hydrolysis of 2-chloropyrimidines 1-3 followed by coupling of the resultant pyrimidin-2(1H)-ones 4-6 with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide under basic conditions (method A) or treatment of 1-3 with potassium trimethylsilanolate followed by coupling of the resultant 2-(trimethylsilyloxy)pyrimidines, without isolation, with β-D-glucose pentaacetate in the presence of tin tetrachloride (method B).",

author = "Abdou, \{Ibrahim M.\} and Lucjan Strekowski and Abdel-Megeed, \{Mohamed F.\} and Attia, \{Adel M.E.\} and Omara, \{Mahmoud A.\}",

year = "1997",

language = "English",

volume = "3",

pages = "295--300",

journal = "Heterocyclic Communications",

issn = "0793-0283",

publisher = "Walter de Gruyter GmbH",

number = "4",

}

TY - JOUR

T1 - Synthesis of 1-(β-D-glucopyranosyl) pyrimidin-2(1H)-ones from 2-chloropyrimidines

AU - Abdou, Ibrahim M.

AU - Strekowski, Lucjan

AU - Abdel-Megeed, Mohamed F.

AU - Attia, Adel M.E.

AU - Omara, Mahmoud A.

PY - 1997

Y1 - 1997

N2 - Tetra-O-acetyl derivatives 10-12 of the title compounds are easily obtained by hydrolysis of 2-chloropyrimidines 1-3 followed by coupling of the resultant pyrimidin-2(1H)-ones 4-6 with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide under basic conditions (method A) or treatment of 1-3 with potassium trimethylsilanolate followed by coupling of the resultant 2-(trimethylsilyloxy)pyrimidines, without isolation, with β-D-glucose pentaacetate in the presence of tin tetrachloride (method B).

AB - Tetra-O-acetyl derivatives 10-12 of the title compounds are easily obtained by hydrolysis of 2-chloropyrimidines 1-3 followed by coupling of the resultant pyrimidin-2(1H)-ones 4-6 with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide under basic conditions (method A) or treatment of 1-3 with potassium trimethylsilanolate followed by coupling of the resultant 2-(trimethylsilyloxy)pyrimidines, without isolation, with β-D-glucose pentaacetate in the presence of tin tetrachloride (method B).

UR - https://www.scopus.com/pages/publications/0007281605

UR - https://www.scopus.com/pages/publications/0007281605#tab=citedBy

M3 - Article

AN - SCOPUS:0007281605

SN - 0793-0283

VL - 3

SP - 295

EP - 300

JO - Heterocyclic Communications

JF - Heterocyclic Communications

IS - 4

ER -

Synthesis of 1-(β-D-glucopyranosyl) pyrimidin-2(1H)-ones from 2-chloropyrimidines

Abstract

ASJC Scopus subject areas

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