16653-52-4

Usage

InChI:InChI=1/C27H44O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)12-21-19-6-5-17-11-18(28)8-9-25(17,3)20(19)13-23(29)26(21,24)4/h15-24,28-29H,5-14H2,1-4H3/t15?,16-,17-,18-,19?,20?,21?,22?,23+,24?,25?,26?,27?/m0/s1

Upstream product

• 467-55-0 hecogenin 
• 915-35-5 hecogenin acetate 
• 863-85-4 3β-acetoxy-12β-hydroxy-5α,25R-spirostan 
• 60-29-7 diethyl ether 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 135707-33-4 C₃₉H₆₄O₁₄ 
• 6877-71-0 isochiapagenin 

Downstream Products

• 5821-04-5 3β,12β-diacetoxy-5α-pregn-16-en-20-one 
• 4235-32-9 C₂₇H₄₂O₄ 
• 1283735-80-7 C₅₅H₈₆O₁₁Si₂ 
• 1283736-14-0 C₅₃H₈₂O₈Si₂ 
• 1283735-98-7 C₅₆H₈₈O₇S₂Si₂ 
• 1283736-00-4 C₅₅H₈₆O₁₁Si₂ 
• 1283735-99-8 C₅₅H₈₄O₉Si₂ 
• 5767-79-3 3β,12β-dihydroxy-5α-pregn-16(17)-ene-20-one 
• 2857-75-2 (R)-4-methyl-δ-valerolactone 

Relevant academic research and scientific papers

A practical synthesis of cephalostatin 1

Let's get practical: A new practical synthetic strategy for natural sterols starting from pregnan-(16S,20S)-diols and steroid-(16S),22-lactones is presented. A tandem double oxymercuration-demercuration and a substitution-ketalization cascade are consider

α,β-epoxy vinyl triflates in Pd-catalyzed reactions

(matrix presented) Reactions of steroidal αβ-epoxy vinyl triflates in Pd-catalyzed reactions are described. Oxidative insertion of Pd0 into the C-O bond, giving vinylpalladium 12, is faster than formation of the π-allyl derivative from the vinyl epoxide. Although 12 can be trapped under certain conditions, it eventually rearranges to palladium alkoxide 14, which is in equilibrium with 15 and/or 10.

Synthesis and biological activity of unsymmetrical bis-steroidal pyrazines related to the cytotoxic marine natural product cephalostatin 1

A mild, high-yielding synthesis of symmetrical steroidal pyrazines was achieved from the dimerization of 2-amino-3-ketosteroids, which were produced in situ from the triphenylphosphine-water reduction of the corresponding α-azido ketone. 2-Azidocholestan-3-one gave the dimeric steroidal pyrrazine very cleanly, and two known dimeric pyrazines based on androstanone were also made using this methodology. Both C2-symmetric geometric isomers of the dimeric steroidal pyrrazine derived from cholestane were prepared by reaction of 2,3-diaminocholestane with cholestane-2,3-dione. A route to unsymmetrical bis-steroidal pyrazines was based on the observation that α-acetoxy ketones react with α-amino oximes directly with no need for oxidation of intermediate dihydropyrazines. Heating either 2β,17β-dihydroxyandrostan-3-one diacetate or 2β,17β-dihydroxyhecogenin-3-one diacetate with 2-amino-3-methoxyiminocholestane in toluene at 145°C gave the corresponding unsymmetrical pyrazine in moderate yield. Five of the steroidal pyrazines were evaluated in the National Cancer Institute's new in vitro, disease-oriented antitumor screen, but none showed sufficient activity to warrant in vivo investigation.

12-Hydroxy steroidal glycosides from the caudex of Yucca gloriosa.

The structures of the new steroidal saponins (tentatively named YS-XI, -XII and -XIII) have been isolated from the caudex of Yucca gloriosa and characterized as 3-O-beta-D-glucopyranosyl-(1----2)-beta-D-galactopyranosyl 5 beta- (25R)-spirostan-3 beta, 12 beta-diol, 3-O-beta-D-glucopyranosyl-(1----2)- [beta-D-glucopyranosyl-(1----3)]-beta-D-glucopyranosyl 5 beta- (25R)-spirostan-3 beta, 12 beta-diol and 3-O-beta-D-glucopyranosyl-(1----2)- beta-D-galactopyranosyl 5 beta-(25R)-spirostan-2 beta,3 beta,12 beta-triol, respectively.