16-(Acetyloxy)-14-hydroxy-3-oxocard-20(22)-enolide

Base Information

• Chemical Name: 16-(Acetyloxy)-14-hydroxy-3-oxocard-20(22)-enolide
• CAS No.: 51227-49-7
• Molecular Formula: C25H34O6
• Molecular Weight: 430.5339
• DSSTox Substance ID: DTXSID30965496
• Mol file: 51227-49-7.mol

Synonyms:DTXSID30965496;LS-52298;16-(Acetyloxy)-14-hydroxy-3-oxocard-20(22)-enolide

Chemical Property of 16-(Acetyloxy)-14-hydroxy-3-oxocard-20(22)-enolide

Chemical Property:

• Vapor Pressure: 4.66E-16mmHg at 25°C
• Boiling Point: 583.8°Cat760mmHg
• Flash Point: 195.5°C
• PSA: 89.90000
• Density: 1.25g/cm³
• LogP: 3.35410
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 430.23553880
• Heavy Atom Count: 31
• Complexity: 862

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CC2(C3CCC4CC(=O)CCC4(C3CCC2(C1C5=CC(=O)OC5)C)C)O
• Isomeric SMILES: CC(=O)O[C@H]1C[C@@]2(C3CC[C@@H]4CC(=O)CC[C@@]4(C3CC[C@@]2(C1C5=CC(=O)OC5)C)C)O

Technology Process of 16-(Acetyloxy)-14-hydroxy-3-oxocard-20(22)-enolide

There total 5 articles about 16-(Acetyloxy)-14-hydroxy-3-oxocard-20(22)-enolide 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: 67.0%

oleandrigenin (465-15-6) → 16β-acetoxy-14-hydroxy-3-oxo-5β,14β-card-20(22)-enolide (51227-49-7)

Guidance literature:

With jones' reagent;

DOI:10.1016/0039-128X(85)90062-5

Reference yield:

→ 16β-acetoxy-14-hydroxy-3-oxo-5β,14β-card-20(22)-enolide (51227-49-7)

Guidance literature:

With chromium(VI) oxide; acetic acid;

DOI:10.1002/hlca.19500330431 DOI:10.1002/hlca.19500330115

Reference yield:

gitoxin (4562-36-1) → 16β-acetoxy-14-hydroxy-3-oxo-5β,14β-card-20(22)-enolide (51227-49-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) pyridine, 2) EtOH, 1 M HCl, reflux

2: 67 percent / Jones' reagent

With jones' reagent;

DOI:10.1016/0039-128X(85)90062-5

upstream raw materials:

acetic anhydride

14,16β-dihydroxy-3-oxo-5β,14β-card-20(22)-enolide

oleandrigenin

gitoxin

Refernces

• 1、 Humber, David C.,Jones, Paul S.,Phillipps, Gordon H.. "SYNTHESIS AND BIOLOGICAL ACTIVITY OF SOME CARDIOTONIC COMPOUNDS RELATED TO GITOXIGENIN". . p. 19 - 30. Retrieved 2007/10/02.