6159-99-5

Upstream product

• 1000612-51-0 C₂₉H₄₃N₃O₃ 
• 1061-54-7 diosgenin acetate 
• 19121-58-5 solasonine 
• 64-19-7 acetic acid 
• 126-17-0 solasodine 
• 108-24-7 acetic anhydride 

Downstream Products

• 126-17-0 solasodine 
• 4860-15-5 solasodine N,O-diacetate 
• 979-02-2 16-dehydropregnenolone acetate 

Relevant academic research and scientific papers

Facile synthesis of solasodine based on a mild halogenation-ring opening reaction of spiroketals in steroidal sapogenins

Herein we report a halogenation-ring opening reaction of spiroketals in steroidal sapogenins at room temperature to gain highly valuable ω-halo enol ethers in excellent yields. Boosted by this method, we have prepared solasodine, an antitumor steroidal alkaloid, from diosgenin acetate in three steps with an overall yield of 50%.

Application of hypoiodite-mediated aminyl radical cyclization to synthesis of solasodine acetate

Solasodine acetate, an anticancer steroidal alkaloid, was synthesized from diosgenin in 8 steps with an overall yield of 23%. A key synthetic step involves the formation of 5/6-oxazaspiroketal moiety via hypoiodite-mediated aminyl radical cyclization of a steroidal primary amine.

NMR Spectra and Stereochemistry of N-Acetyl and N-Benzoyl Derivatives of Solasodine

N-Acetylation of solasodine gives only one rotameric N-acetyl derivative compared with N-acetyl-3-methylpiperidine, which exists in solution as two equally populated rotamers.The 1H and 13C NMR spectra (CDCl3) of O,N-diacetyl- and O-acetyl-N-benzoylsolasodine indicate significant deviations from F-ring chair geometry.Opening of the F ring of these derivatives in CDCl3 solution at 25 deg C, to give the corresponding furosta-5,20(22)-diene derivatives, was ascertained by NMR spectroscopy.Key Words: Solasodine O,N-Diacetylsolasodine O-Acetyl-N-benzoylsolasodine 3β-Acetoxy-26-acetamidofurosta-5,20(22)-diene 3β-Acetoxy-26-benzamidofurosta-5,20(22)-diene