From Chlorobenzene to a Carbohydrate in Two Steps. A New Chemoenzymatic Synthesis of 2,3-O-Isopropylidene-D-erythruronolactone

[img]PDF - Authorized users only
Language: English
378Kb
Title:From Chlorobenzene to a Carbohydrate in Two Steps. A New Chemoenzymatic Synthesis of 2,3-O-Isopropylidene-D-erythruronolactone
Creators:
Mandel, Martin
Hudlický, Tomáš
Kwart, Lawrence D.
Whited, Gregg M.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 58, 10, pp. 2517-2522

Abstract

Controlled oxidation of chloroepoxide <i>V</i> with two equivalents of sodium periodate furnished 2,3-<i>O</i>-isopropylidene-D-erythruronolactone (<i>I</i>) in 63% yield. This procedure was augmented by combining the protection of diol <i>III</i>, the oxidation of acetonide <i>IV</i> to <i>V</i>, and the subsequent oxidative cleavage to <i>I</i> into one operation which yielded, on medium scale, the title lactone in 51% yield. detailed procedure of preparation and physical constants are provided for lactone <i>I</i>.

Title:From Chlorobenzene to a Carbohydrate in Two Steps. A New Chemoenzymatic Synthesis of 2,3-O-Isopropylidene-D-erythruronolactone
Creators:
Mandel, Martin
Hudlický, Tomáš
Kwart, Lawrence D.
Whited, Gregg M.
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:58
Number:10
Page Range:pp. 2517-2522
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19932517UNSPECIFIED
ID Code:367
Item Type:Article
Deposited On:06 Feb 2009 17:00
Last Modified:06 Feb 2009 16:00

Citation

Mandel, Martin; Hudlický, Tomáš; Kwart, Lawrence D.; Whited, Gregg M. (1993) From Chlorobenzene to a Carbohydrate in Two Steps. A New Chemoenzymatic Synthesis of 2,3-O-Isopropylidene-D-erythruronolactone. Collection of Czechoslovak Chemical Communications, 58 (10). pp. 2517-2522. ISSN 0010-0765

Repository Staff Only: item control page