514-33-0

Usage

Uses

Used in Pharmaceutical Industry:
(20S)-3β,16β-Dihydroxy-5α-pregnane-20-carboxylic acid γ-lactone is used as a pharmaceutical agent for its potential hormone regulation and reproductive function effects. Its ability to modulate hormone levels and influence reproductive processes makes it a promising candidate for the development of medications targeting hormonal imbalances and fertility issues.
Used in Research Applications:
In the field of scientific research, (20S)-3β,16β-Dihydroxy-5α-pregnane-20-carboxylic acid γ-lactone serves as a valuable tool for studying the mechanisms of hormone regulation and the role of steroids in reproductive function. Its unique structure and potential biological activity provide researchers with insights into the complex interactions between hormones and their target tissues, contributing to a better understanding of related physiological processes.
Further research is needed to fully understand the properties and potential uses of (20S)-3β,16β-Dihydroxy-5α-pregnane-20-carboxylic acid γ-lactone in medicine and other fields. Its exploration may lead to the discovery of new therapeutic applications and a deeper comprehension of the underlying biological processes.

InChI:InChI=1/C22H34O3/c1-12-19-18(25-20(12)24)11-17-15-5-4-13-10-14(23)6-8-21(13,2)16(15)7-9-22(17,19)3/h12-19,23H,4-11H2,1-3H3/t12-,13-,14-,15+,16-,17-,18-,19-,21-,22-/m0/s1

Upstream product

• 96065-39-3 16β-hydroxy-3-oxo-23,24-dinor-chol-4-en-22-oic acid-lactone 
• 126-18-1 smilagenin 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 6870-74-2 Dihydrosarsasapogenin 
• 359416-36-7 3β-acetoxy-16β-hydroxy-5β-bisnorcholanoic acid 22->16 lactone 
• 77-60-1 tigogenin 
• 481-29-8 Epiandrosterone 
• 216572-49-5 (S)-2-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-16-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-propionitrile 
• 216572-48-4 (3β,5α,17E)-3-{[(tert-butyl)dimethylsilyl]oxy}-pregn-17(20)-en-16-one 
• 216572-47-3 (3β,5α,16α,17E)-3-{[(tert-butyl)dimethylsilyl]oxy}-pregn-17(20)-en-16-ol 
• 216572-46-2 (3β,5α,17Z)-3-{[(tert-butyl)dimethylsilyl]oxy}-21-pregn-17(20)-ene 
• 57711-44-1 (3S,10S,13S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta-[a]phenanthren-17-one 
• 216572-50-8 (S)-2-[(3S,5S,8R,9S,10S,13S,14S,16S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-16-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-propionitrile 

Downstream Products

• 1584133-07-2 C₃₈H₅₂O₃Si 
• 1584133-11-8 C₃₈H₅₄O₃Si 

Relevant academic research and scientific papers

Synthesis of "glycospirostanes" via ring-closing metathesis

Syntheses of "glycospirostanes" from 3β-hydroxy-23,24-dinor-5α-cholano-22,16-lactone and 3α-hydroxy-23,24-dinor-5β-cholano-22,16-lactone were performed. The key step of these syntheses was ring-closing metathesis of the corresponding C,O-diallyl derivativ

A Convenient Synthesis of (16S,20S)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its N-alkyl Derivatives

A concise synthesis of (16S,20S)-3β-hydroxy-5α-pregnane-20,16-carbolactam from tigogenin via the corresponding lactone is described. The most efficient synthetic route consisted of the lactone ring-opening with aminoalane reagent followed by PDC or Dess-Martin oxidation. The oxo-amide obtained was subjected to cyclization with Et3SiH/TFA or Et3SiH/Bi(TfO)3. Alternately, the lactone was converted first to the oxo-acid, which was then subjected to the microwave-assisted reductive amination. N-Alkyl derivatives were also obtained in a similar way.

Stereospecific synthesis of steroidal 20,16-γ-carbolactones

Two strategies have been explored for the synthesis of steroidal 20,16- γ-carbolactones from the corresponding 17-ketoandrostane. A highly efficient, stereospecific protocol has been developed for the β-oriented cis-γ-lactone, based on a Michael addition of cyanide to a conjugated ketone. A different approach, involving prior attachment of a 3-carbon side chain on C-17 of a 17-oxo-16β-acetoxy-androstane led to the epimeric, α- oriented lactone.

Mechanistic studies of the rearrangements of steroidal 16,17-ketols and syntheses of 20→16-cis-γ-carbolactones

Utilization of 17-keto-androstanes as starting materials for the synthesis of α- or β-oriented steroidal 20→16-γ-carbolactones has been explored following two different strategies. A highly efficient, stereospecific protocol has been developed for the β-oriented cis-γ-lactone. A different approach, involving prior attachment of a 3-carbon side chain on C-17 of a 17-oxo-16β-acetoxy-androstane led to the epimeric, α-oriented lactone. The mechanism of the rearrangement of epimeric 16β- or 16α-hydroxy-17-keto-androstanes to 17β-hydroxy-16-keto-androstanes was studied by 13C NMR spectroscopy. The former occurs through a 1,2-sigmatropic H-shift, while the latter is likely to take place by simple enolization-reprotonation. Copyright (C) 1999 Elsevier Science Ltd.

Access to 27-Nortomatidine and 27-Norsoladulcidine Derivatives

Synthesis of (22R)- and (22S)-27-norspirosolane alkaloids from tigogenin, epismilagenin, and smilagenin is described. The alkaloids were prepared from readily available dinorcholanic lactones via their reaction with 4-chlorobutyllithium followed by substi

Highly efficient and scalable synthesis of clionamine D

Herein we describe an efficient and scalable synthesis of clionamine D (4), a special member with autophagy bioactivity and an unprecedented spirobislactone side chain in the novel aminosteroid clionamines. This synthesis features a quick access to α-methylene-γ-lactone 8 and a Mn(OAc)3-mediated radical [3 + 2] reaction to assemble the unique spirobislactone unit. Clionamine D (4) can also serve as a key synthetic precursor to other clionamine members.