Alkylation of Partially Protected Xylofuranoses and Tetritols with (2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoroheptyl)oxirane and the Stability of Protecting Acetal Groups Towards Lewis Acid-Type Catalyst

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Title:Alkylation of Partially Protected Xylofuranoses and Tetritols with (2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoroheptyl)oxirane and the Stability of Protecting Acetal Groups Towards Lewis Acid-Type Catalyst
Creators:
Kefurt, Karel
Moravcová, Jitka
Bambasová, Šárka
Buchalová, Kateřina
Vymětalíková, Barbora
Kefurtová, Zdeňka
Staněk, Jan
Paleta, Oldřich
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 66, 11, pp. 1665-1681
Uncontrolled Keywords:Oxygen carriers, Fluoroalkylated epoxides, Fluorinated sugars, Lewis acid catalysis, Ring opening, Fluoroalkylations, Fluorophilic sugars, Carbohydrates

Abstract

1,2-<i>O</i>-Isopropylidene-3-<i>O</i>-methyl-α-D-xylofuranose (<strong>2</strong>), 1,2-<i>O</i>-isopropylidene-α-D-xylofuranose (<strong>3</strong>), 2,4-<i>O</i>-ethylidene-D-erythritol (<strong>4</strong>) and 1,3-<i>O</i>-ethylidene-D-threitol (<strong>5</strong>) were alkylated with racemic (2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptyl)oxirane (<strong>1</strong>) using boron trifluoride diethyl etherate as a catalyst. The desired mono- or disubstituted polyfluoroalkyl derivatives <strong>6</strong>-<strong>11</strong> were isolated only in low to medium yields. The fluoroalkylation was accompanied with disproportional distributions of the protecting acetal/ketal groups and polymerization of saccharides. Therefore the stability of <strong>3</strong>, <strong>4</strong>, <strong>5</strong>, 5-<i>O</i>-acetyl-1,2-<i>O</i>-isopropylidene-α-D-xylofuranose (<strong>14</strong>) and 1,2-<i>O</i>-isopropylidene-α-D-glucofuranose (<strong>15</strong>) in the presence of a catalytic amount of boron trifluoride diethyl etherate was investigated in various solvents. A mechanism explaining the effect of the catalyst has been proposed. <p>

Title:Alkylation of Partially Protected Xylofuranoses and Tetritols with (2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoroheptyl)oxirane and the Stability of Protecting Acetal Groups Towards Lewis Acid-Type Catalyst
Creators:
Kefurt, Karel
Moravcová, Jitka
Bambasová, Šárka
Buchalová, Kateřina
Vymětalíková, Barbora
Kefurtová, Zdeňka
Staněk, Jan
Paleta, Oldřich
Uncontrolled Keywords:Oxygen carriers, Fluoroalkylated epoxides, Fluorinated sugars, Lewis acid catalysis, Ring opening, Fluoroalkylations, Fluorophilic sugars, 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:66
Number:11
Page Range:pp. 1665-1681
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20011665UNSPECIFIED
ID Code:1884
Item Type:Article
Deposited On:06 Feb 2009 17:13
Last Modified:06 Feb 2009 16:13

Citation

Kefurt, Karel; Moravcová, Jitka; Bambasová, Šárka; Buchalová, Kateřina; Vymětalíková, Barbora; Kefurtová, Zdeňka; Staněk, Jan; Paleta, Oldřich (2001) Alkylation of Partially Protected Xylofuranoses and Tetritols with (2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoroheptyl)oxirane and the Stability of Protecting Acetal Groups Towards Lewis Acid-Type Catalyst. Collection of Czechoslovak Chemical Communications, 66 (11). pp. 1665-1681. ISSN 0010-0765

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