Calliterpenone

Base Information

• Chemical Name: Calliterpenone
• CAS No.: 38602-53-8
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.472
• Mol file: 38602-53-8.mol

Synonyms:(16R)-16,17-dihydroxy-ent-kauran-3-one;Abbeokuton;

Chemical Property of Calliterpenone

Chemical Property:

• PSA: 57.53000
• LogP: 3.32160

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Calliterpenone

There total 10 articles about Calliterpenone 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: 38.0%

(16R)-16,17-epoxy-ent-kauran-3-one (548486-51-7) → (16R)-16,17-dihydroxy-ent-kauran-3-one (38602-53-8,131830-94-9,135683-73-7,16836-28-5) + ent-16,17-dihydroxy-16β-kauran-3-one (16836-28-5,38602-53-8,131830-94-9,135683-73-7) + (16R)-3-oxo-ent-kauran-17-al + 17-hydroxy-ent-kaur-15-en-3-one

Guidance literature:

With sulfuric acid; In tetrahydrofuran; water; at 20 ℃; Further byproducts given;

DOI:10.1002/hlca.200390043

Reference yield: 38.0%

(16R)-16,17-epoxy-ent-kauran-3-one (548486-51-7) → (16R)-16,17-dihydroxy-ent-kauran-3-one (38602-53-8,131830-94-9,135683-73-7,16836-28-5) + ent-16,17-dihydroxy-16β-kauran-3-one (16836-28-5,38602-53-8,131830-94-9,135683-73-7) + (16R)-3-oxo-ent-kauran-17-al + 17-hydroxy-ent-kaur-15-en-3-one

Guidance literature:

With sulfuric acid; In tetrahydrofuran; water; at 20 ℃; Further byproducts given;

DOI:10.1002/hlca.200390043

Reference yield:

(16R)-16,17-dihydroxy-ent-kauran-3-one (38602-53-8,131830-94-9,135683-73-7,16836-28-5) → ent-16,17-dihydroxy-16β-kauran-3-one (16836-28-5,38602-53-8,131830-94-9,135683-73-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / pyridine / 20 °C

2: 95 percent / K₂CO₃ / methanol / 20 °C

3: 4 percent / 5 percent H₂SO₄ / tetrahydrofuran; H₂O / 20 °C

With pyridine; sulfuric acid; potassium carbonate; In tetrahydrofuran; methanol; water;

DOI:10.1002/hlca.200390043

upstream raw materials:

ent-17-acetoxy-16β-hydroxykauran-3-one

ent-kaurene-16-en-3-one

(16R)-16,17-epoxy-ent-kauran-3-one

(16R)-16-hydroxy-17-{[(4-methylphenyl)sulfonyl]oxy}-ent-kauran-3-one

Downstream raw materials:

ent-16,17-dihydroxy-16β-kauran-3-one

(16R)-16-hydroxy-17-{[(4-methylphenyl)sulfonyl]oxy}-ent-kauran-3-one

C₂₀H₃₄O₃

Refernces

• 1、 Liu, Gui,Mueller, Ralph,Rueedi, Peter. "Chemical transformations of phyllocladane (=13β-kaurane) diterpenoids". . p. 420 - 438. Retrieved 2007/10/03.