16-DPA
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| Chemical formula | C23H32O3 |
|---|---|
| OTP appearance | white crystalline powder |
| Molar Mass(g/mol) | 356.506 |
| Melting Point(°C) | 171-172 |
| NFPA 704 |  0
0
0
|
16-Dehydropregnenolone acetate (16-DPA) is a core structure (synthon) in the production of many semisynthetic steroidal compounds. As 7-ACA is for cephalosporins and 6-APA is for penicillins, 16-DPA is for steroids. While it is not easy to synthesize, it is a convenient intermediate which can be made from other more available materials, and which can then be modified to produce the desired target compound.
Uses
Primary
- Production of corticosteroid medicines
Natural occurrence
Hazards
Production
Synthesis
from diosgenin
Three methods starting from diosgenin.[1] [2][3] from mexican yams
from solanidine
From solanidine from potatos.[4] File:Solanidine to 16-DPA.png
In 1997 Gaši et al. reported[5] a short procedure for the degradation of solanidine to DPA.
- Instead of applying the electrochemical oxidation, Hg(OAc)2 in acetone was used as oxidizing agent. The advantage of this reagent and solvent system was the ease of use and the selective formation of the iminium salt 2, which spontaneously isomerized to enamine 3 (94%).
- This enamine was then subjected to another isomerization, which yielded the more thermodynamically more stable enamine 4.
- Sodium iodate-oxidation opened up the cyclic enamine and gave lactam 5.
- Elimination of the lactam part with aluminum oxide in benzene afforded in 34% 16-dehydropregnenolone acetate (DPA) (6).
Testing
Purification
Storage
Disposal
See Also
References
- ↑ Mancino, Valentina; Cerra, Bruno; Piccinno, Alessandro; Gioiello, Antimo (2018) "Continuous Flow Synthesis of 16-Dehydropregnenolone Acetate, a Key Synthon for Natural Steroids and Drugs".
Organic Process Research & Development 22(5); pp600-607.
DOI:10.1021/acs.oprd.8b00038 - ↑ Chowdhury, Pritish; Borah, Juri Moni; Bordoloi, Manobjyoti; et al (2011) "A Simple Efficient Process for the Synthesis of 16-DPA from Diosgenin" (local copy)
Journal of Chemical Engineering & Process Technology 2(5)
link courtesy Researchgate. - ↑ Goswami, Amrit; Kotoky, Rumi; Rastogi, Romesh C.; et al (2003) "A One-Pot Efficient Process for 16-Dehydropregnenolone Acetate"
Organic Process Research and Development 7(3); pp306-308.
DOI:10.1021/op0200625
link courtesy ACS. - ↑ Vronen, Patrick J.E.; Koval, Nadeshda; de Groot, Aede "The synthesis of 16-dehydropregnenolone acetate (DPA) from potato glycoalkaloids"
DOI:10.3998/ark.5550190.0005.203 - ↑ CAŠI, KATARINA T. M. PENOV (1997) "L6-Dehydropregnenolone acetate from solanidine"
J. Serb. Chem. Soc 62(6); pp451-454.