(3beta,5alpha,12beta,25R)-3,12-di(acetoxy)-spirostan-11-one

Base Information

• Chemical Name: (3beta,5alpha,12beta,25R)-3,12-di(acetoxy)-spirostan-11-one
• CAS No.: 82182-52-3
• Molecular Formula: C₃₁H₄₆O₇
• Molecular Weight: 530.702
• NSC Number: 80699
• Mol file: 82182-52-3.mol

Synonyms:NSC80699;SCHEMBL8501933;SJZHCCUPAKHVFK-HVOGIZCUSA-N;NSC-80699;(3beta,5alpha,12beta,25R)-3,12-di(acetoxy)spirostan-11-one;(3beta,5alpha,12beta,25R)-3,12-di(acetoxy)-spirostan-11-one;82182-52-3

Chemical Property of (3beta,5alpha,12beta,25R)-3,12-di(acetoxy)-spirostan-11-one

Chemical Property:

• Vapor Pressure: 2.87E-14mmHg at 25°C
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 530.32435380
• Heavy Atom Count: 38
• Complexity: 1010

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCC2(C(C3C(O2)CC4C3(C(C(=O)C5C4CCC6C5(CCC(C6)OC(=O)C)C)OC(=O)C)C)C)OC1
• Isomeric SMILES: C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3([C@@H](C(=O)[C@H]5[C@H]4CC[C@@H]6[C@@]5(CC[C@@H](C6)OC(=O)C)C)OC(=O)C)C)C)OC1

Technology Process of (3beta,5alpha,12beta,25R)-3,12-di(acetoxy)-spirostan-11-one

There total 16 articles about (3beta,5alpha,12beta,25R)-3,12-di(acetoxy)-spirostan-11-one 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: 93.0%

acetic anhydride (108-24-7) + 3β,12β-dihydroxy-11-oxo-(25R)-5α-spirostane (86023-87-2) → (3β,5α,12β,25R)-3,12-di(acetoxy)spirostan-11-one (82182-52-3)

Guidance literature:

With pyridine; In water;

DOI:10.1021/jm960123n

Reference yield:

3β-acetoxy-11α,23α-dibromo-12-oxo-(25R)-5α-spirostane (5130-60-9) → (3β,5α,12β,25R)-3,12-di(acetoxy)spirostan-11-one (82182-52-3)

Guidance literature:

With potassium hydroxide; Behandeln des Reaktionsprodukts mit Perchlorsaeure enthaltendem Acetanhydrid und Erhitzen des danach isolierten Reaktionsprodukts mit Essigsaeure und Zink-Pulver;

DOI:10.1021/ja01621a054

Reference yield:

hecogenin acetate (915-35-5) → (3β,5α,12β,25R)-3,12-di(acetoxy)spirostan-11-one (82182-52-3)

Guidance literature:

Multi-step reaction with 3 steps

1: chloroform; bromine / Behandeln des Reaktionsprodukts mit methanol. Kalilauge und anschliessendem Erwaermen mit Kaliumhydroxid

2: acetic acid; zinc-powder

3: perchloric acid; acetic acid

With perchloric acid; chloroform; bromine; acetic acid; zinc;

DOI:10.1021/ja01116a002

upstream raw materials:

(25R)-3β,12β-Diacetoxy-5α-spirostan-11α-ol

(23S,25R)-3β,12β-diacetoxy-23-bromo-5α-spirostan-11-one

acetic anhydride

3β,12β-dihydroxy-11-oxo-(25R)-5α-spirostane

Downstream raw materials:

3β,11α-dihydroxy-(25R)-5α-spirostane

11-ketotigogenin

3β,12β-dihydroxy-11-oxo-(25R)-5α-spirostane

3β-acetoxy-5α,25R-spirostan-11-one