Etienic etienate as synthon for the synthesis of steroid oligoester gelators.
Linear oligoesters based on etienic acid (3beta-hydroxyandrost-5-ene-17beta-carboxylic acid) containing four steroid units were prepared using a 2+2 synthetic strategy in a successful synthesis of 3beta-{[3beta-({3beta-[(3beta-hydroxyandrost-5-ene-17beta-carbonyl)oxy]androst-5-ene-17beta-carbonyl}oxy)androst-5-ene-17beta-carbonyl]oxy}androst-5-ene-17beta-carboxylic acid. The main problems with deprotection were overcome by using orthogonal groups as O-nitrates and 2-(trimethylsilyl)ethyl ethers.
Drasar
Pavel
P
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo ndm. 2, CZ-166 10 Prague 6, Czech Republic. pavel.drasar@vscht.cz
Budesínský
Milos
M
Reschel
Miroslav
M
Pouzar
Vladimír
V
Cerný
Ivan
I
D000736:Androstenes / Q000737:chemistry*; D004951:Esterification; D004952:Esters / Q000737:chemistry; D005782:Gels / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D013055:Spectrophotometry, Infrared
D000736:Androstenes; D004952:Esters; D005782:Gels; D011108:Polymers; C004251:etienic acid