Synthesis of 5α-Cholestane Type Glycoside Sulfates

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Title:Synthesis of 5α-Cholestane Type Glycoside Sulfates
Creators:
Arnoštová, Libuše
Černý, Ivan
Pouzar, Vladimír
Drašar, Pavel
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 58, 5, pp. 1180-1190

Abstract

Synthesis of steroid glycoside sulfates sulfated both on the steroid skeleton and in sugar part are presented. Sodium salts of 5α-cholestane-3β,6α-diol 6-β-D-glucoside 3-sulfate <i>V</i> and 3-β-D-glucoside 6-sulfate <i>XI</i> were prepared from 3β-(2-tetrahydropyranyloxy)-5α-cholestan-6α-ol (<i>I</i>) using acetyl and methoxymethyl groups for temporary protection. Sulfation in the sugar part was at first checked in pregnane series and triethylammonium salts of 3β-(β-D-glucopyranosyloxy)pregn-5-en-20-one 6'-sulfate (<i>XXVI</i>) and 4'-sulfate 2',3'-diacetate <i>XXVII</i> were prepared. Application of the method on cholestane derivatives gave triethylammonium salt of 5α-cholestan-3β-yl β-D-glucopyranoside-6-sulfate (<i>XXXI</i>).

Title:Synthesis of 5α-Cholestane Type Glycoside Sulfates
Creators:
Arnoštová, Libuše
Černý, Ivan
Pouzar, Vladimír
Drašar, Pavel
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:5
Page Range:pp. 1180-1190
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19931180UNSPECIFIED
ID Code:234
Item Type:Article
Deposited On:06 Feb 2009 16:59
Last Modified:06 Feb 2009 15:59

Citation

Arnoštová, Libuše; Černý, Ivan; Pouzar, Vladimír; Drašar, Pavel (1993) Synthesis of 5α-Cholestane Type Glycoside Sulfates. Collection of Czechoslovak Chemical Communications, 58 (5). pp. 1180-1190. ISSN 0010-0765

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