Etienic etienate as synthon for the synthesis of steroid oligoester gelators

Pavel Drasar; Milos Budesínský; Miroslav Reschel; Vladimír Pouzar; Ivan Cerný

doi:10.1016/j.steroids.2005.02.021

Etienic etienate as synthon for the synthesis of steroid oligoester gelators

Steroids. 2005 Aug;70(9):615-25. doi: 10.1016/j.steroids.2005.02.021.

Authors

Pavel Drasar¹, Milos Budesínský, Miroslav Reschel, Vladimír Pouzar, Ivan Cerný

Affiliation

¹ Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo ndm. 2, CZ-166 10 Prague 6, Czech Republic. [email protected]

PMID: 15907964
DOI: 10.1016/j.steroids.2005.02.021

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Androstenes / chemistry*
Esterification
Esters / chemistry
Gels / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Polymers / chemical synthesis*
Polymers / chemistry
Spectrophotometry, Infrared

Substances

Androstenes
Esters
Gels
Polymers
etienic acid