Synthesis of some 16,17-secoandrost-5-ene derivatives
| Autor: | N Marija Sakac, M Katarina Penov-Gasi, A Evgenija Djurendic, R Andrea Gakovic, Maja Djurendic-Brenesel Dj. |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2010 |
| Předmět: |
Stereochemistry
General Chemical Engineering Ms analysis Oppenauer oxidation Alcohol General Chemistry Formyl group 16 17-seco steroids lcsh:Chemical technology Medicinal chemistry Reaction product chemistry.chemical_compound chemistry Derivative (finance) Yield (chemistry) reduction of aldehydes androst-5-ene derivatives lcsh:TP1-1185 Ene reaction |
| Zdroj: | Hemijska Industrija, Vol 64, Iss 2, Pp 81-84 (2010) |
| Popis: | Starting from 3?-acetoxy-17-oxo-16,17-secoandrost-5-ene-16-nitrile (1), 3?-acetoxy-16,17-secoandrost-5-ene-16-nitrile (4) was synthesized by a three-stage procedure. First, the formyl group of compound 1 was reduced, to yield the alcohol 2. Compound 2 was further transformed to the mesyloxy derivative 3, whose reduction with NaBH3CN gave compound 4. Apart from compound 4 as the main reaction product, two additional products were obtained, for which the GC/MS analysis suggested that they are 8(14) and 14 derivatives of compound 4. Compound 4 was transformed into 3?-hydroxy-16,17-sesoandrost-5-ene-16-nitrile (7), the Oppenauer oxidation of which afforded 3-oxo-16,17-secoandrost-4-ene-16-nitrile (8). |
| Databáze: | OpenAIRE |
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