Amphiphilic Perfluoroalkylated Derivatives of Aliphatic Triols: Hemocompatibility and Effect on Perfluorocarbon Emulsion

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Title:Amphiphilic Perfluoroalkylated Derivatives of Aliphatic Triols: Hemocompatibility and Effect on Perfluorocarbon Emulsion
Creators:
Církva, Vladimír
Kaplánek, Robert
Paleta, Oldřich
Kodíček, Milan
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 10, pp. 1436-1448
Uncontrolled Keywords:Oxygen carriers, Hemocompatibility, Regioselectivity of fluoroalkylations, Fluoroalkylations, Perfluoroalkyl epoxides, Blood substituents, Fluorinated surfactants, Fluorophilic triols

Abstract

Two sets of amphiphilic perfluoroalkylated aliphatic triols were prepared in a two-step synthesis: a protected glycerol, 4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane (<strong>1</strong>) and protected 2-hydroxymethyl-2-methylpropane-1,3-diol, 5-hydroxymethyl-2,2,5-trimethyl-1,3-dioxane (<strong>11</strong>) were fluoroalkylated with racemic 2-(2,2,3,3,4,4,5,5,5-nonafluoropentyl)- (<strong>2</strong>), or 2-(2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptyl)- (<strong>3</strong>) or 2-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononyl)oxirane (<strong>4</strong>) using boron trifluoride diethyl etherate as a catalyst to afford intermediates <strong>5</strong>-<strong>7</strong> and <strong>12</strong>-<strong>14</strong>, which were deprotected by re-acetalization to the target&nbsp;triols HOCH<sub>2</sub>CH(OH)CH<sub>2</sub>OCH<sub>2</sub>CH(OH)CH<sub>2</sub>CF<sub>2</sub>(CF<sub>2</sub>)<i><sub>n</sub></i>CF<sub>3</sub> (<i>n</i> = 2, 4, 6) <strong>8</strong>-<strong>10</strong> and (OHCH<sub>2</sub>)<sub>2</sub>C(CH<sub>3</sub>)CH<sub>2</sub>OCH<sub>2</sub>CH(OH)CH<sub>2</sub>CF<sub>2</sub>(CF<sub>2</sub>)<i><sub>n</sub></i>CF<sub>3</sub> (<i>n</i> = 2, 4, 6) <strong>15</strong>-<strong>17</strong>. Regioselectivity of competitive fluoroalkylation of propane-1,2-diol and butane-1,3-diol appeared to be considerably dependent on the catalyst up to 93 rel.% for the preferential fluoroalkylation at the primary hydroxy group. Hemocompatibility of the triols <strong>8</strong>-<strong>10</strong> and <strong>15</strong>-<strong>17</strong>, which was very high for linear-chain amphiphiles <strong>9</strong> and <strong>10</strong>, showed particular dependence on the starting triol and perfluoroalkyl-chain length. All amphiphiles <strong>8</strong>-<strong>10</strong> and <strong>15</strong>-<strong>17</strong> displayed very good compatibility with perfluorodecalin-Pluronic F-68 water emulsion. <p>

Title:Amphiphilic Perfluoroalkylated Derivatives of Aliphatic Triols: Hemocompatibility and Effect on Perfluorocarbon Emulsion
Creators:
Církva, Vladimír
Kaplánek, Robert
Paleta, Oldřich
Kodíček, Milan
Uncontrolled Keywords:Oxygen carriers, Hemocompatibility, Regioselectivity of fluoroalkylations, Fluoroalkylations, Perfluoroalkyl epoxides, Blood substituents, Fluorinated surfactants, Fluorophilic triols
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:67
Number:10
Page Range:pp. 1436-1448
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20021436UNSPECIFIED
ID Code:2005
Item Type:Article
Deposited On:06 Feb 2009 17:14
Last Modified:06 Feb 2009 16:14

Citation

Církva, Vladimír; Kaplánek, Robert; Paleta, Oldřich; Kodíček, Milan (2002) Amphiphilic Perfluoroalkylated Derivatives of Aliphatic Triols: Hemocompatibility and Effect on Perfluorocarbon Emulsion. Collection of Czechoslovak Chemical Communications, 67 (10). pp. 1436-1448. ISSN 0010-0765

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