spirosolan-3-yl acetate

Base Information

• Chemical Name: spirosolan-3-yl acetate
• CAS No.: 66934-60-9
• Molecular Formula: C₂₉H₄₇NO₃
• Molecular Weight: 457.697
• Mol file: 66934-60-9.mol

Synonyms:tomatidine acetate

Chemical Property of spirosolan-3-yl acetate

Chemical Property:

• Vapor Pressure: 1.25E-11mmHg at 25°C

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of spirosolan-3-yl acetate

There total 19 articles about spirosolan-3-yl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C29H47NO3 → (22R,25R)-3β-acetoxy-(5α)-spirosolane (66934-60-9) + tomatidine acetate (66934-60-9)

Guidance literature:

With chloro-trimethyl-silane; In acetonitrile; at 23 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/ejoc.202000051

Reference yield:

C29H47NO3 → (22R,25R)-3β-acetoxy-(5α)-spirosolane (66934-60-9) + tomatidine acetate (66934-60-9)

Guidance literature:

With chloro-trimethyl-silane; In acetonitrile; at 23 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/ejoc.202000051

Reference yield:

(4S,5′S,6aS,8aS,9S,10R,11aS)-5′,6a,8a,9-tetramethyldocosahydrospiro[naphtho[2′,1′:4,5]indeno[2,1-b]furan-10,2′-pyran]-4-yl acetate (4948-43-0) → tomatidine acetate (66934-60-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium bromide; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 3 h / 23 °C / Inert atmosphere

2.1: N,N-dimethyl-formamide / 2 h / 70 °C / Inert atmosphere

2.2: 70 °C / Inert atmosphere

3.1: sodium iodide / acetonitrile / 0.5 h / Inert atmosphere

4.1: chloro-trimethyl-silane / acetonitrile / 0.5 h / 23 °C / Inert atmosphere

With chloro-trimethyl-silane; boron trifluoride diethyl etherate; sodium iodide; lithium bromide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.202000051

upstream raw materials:

acetic anhydride

soladulcidine

solasodine

(4S,5′S,6aS,8aS,9S,10R,11aS)-5′,6a,8a,9-tetramethyldocosahydrospiro[naphtho[2′,1′:4,5]indeno[2,1-b]furan-10,2′-pyran]-4-yl acetate

Downstream raw materials:

tomatidine

Refernces

• 1、 Normandin, Chad,Malouin, Fran?ois,Marsault, Eric. "Gram-Scale Synthesis of Tomatidine, a Steroid Alkaloid with Antibiotic Properties Against Persistent Forms of Staphylococcus aureus". . p. 2693 - 2698. Retrieved 2020/05/04.