Homologation of O-Acetylated Methyl Hexopyranosides with a Grignard C1 Reagent

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Title:Homologation of O-Acetylated Methyl Hexopyranosides with a Grignard C1 Reagent
Creators:
Grzeszczyk, Barbara
Zamojski, Aleksander
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 4, pp. 610-620
Uncontrolled Keywords:Grignard reagents, Homologation reactions, Heptoses, Additions, Heptopyranosides, Allyloxymethylmagnesium chloride, Aldehydes, Carbohydrates

Abstract

Three methyl 2,3,4-tri-<i>O</i>-acetyl-α-D-hexopyranosides of the <i>manno</i>, <i>gluco</i>, and <i>galacto</i> configuration were oxidized to the corresponding methyl hexodialdo-1,5-pyranosides and then reacted with allyloxymethylmagnesium chloride. Methyl heptopyranosides of the D- and L-<i>glycero</i>-α-D-<i>manno</i>-, -α-D-<i>gluco</i>, and -α-D-<i>galacto</i> configuration were obtained in moderate yields. Migration of the 4-<i>O</i>-acetyl group in the products was observed. An interpretation of the results was proposed. <p>

Title:Homologation of O-Acetylated Methyl Hexopyranosides with a Grignard C1 Reagent
Creators:
Grzeszczyk, Barbara
Zamojski, Aleksander
Uncontrolled Keywords:Grignard reagents, Homologation reactions, Heptoses, Additions, Heptopyranosides, Allyloxymethylmagnesium chloride, Aldehydes, Carbohydrates
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:65
Number:4
Page Range:pp. 610-620
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20000610UNSPECIFIED
ID Code:1665
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Grzeszczyk, Barbara; Zamojski, Aleksander (2000) Homologation of O-Acetylated Methyl Hexopyranosides with a Grignard C1 Reagent. Collection of Czechoslovak Chemical Communications, 65 (4). pp. 610-620. ISSN 0010-0765

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