A Solution-Phase Combinatorial Parallel Synthesis of 3β-Amido-3α-hydroxy-5α-androstane-17-ones. -A two-level library of title compounds (IV) is prepared via reaction of oxirane (I) with 4 primary amines followed by treatment of each set with 4 aliphatic acyl chlorides. The purities of the products
A solution-phase combinatorial parallel synthesis of 3β-amido-3α-hydroxy-5α-androstane-17-ones
✍ Scribed by Rene´ Maltais; Donald Poirier
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 204 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A two-level library of 313-amido-3t~-hydroxy-5ct-androstane-17-one compounds was synthesized from a steroid precursor using the solution-phase parallel s),nthesis. The compounds were easily obtained in high purity by regioselective aminolysis of the oxwane intermediate followed by aeylation of the amine. Since oxiranes can begenerated from readily available ketones or alkenes, the proposed strategy give access to a large seres of compounds.
📜 SIMILAR VOLUMES
The ring conformation of the title compound, C 19 H 30 O 3 , is similar to that of the 5-epimer except for the cis A/B ring junction. Ring D adopts a 13,14-half chair conformation. The molecules are linked together by a two-dimensional network of hydrogen bonds involving the carbonyl and hydroxyl gr
In the title molecule, C~21~H~31~ClO~4~, rings __A__, __B__ and __C__ have regular chair conformations, while ring __D__ has an envelope form. In the crystal structure, weak intermolecular C—H...O hydrogen bonds link the molecules into zigzag chains running along the __b__ axis.
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