9-Z-(3R,3'R)-diatoxanthin

Base Information

• Chemical Name: 9-Z-(3R,3'R)-diatoxanthin
• CAS No.: 70267-38-8
• Molecular Formula: C₄₀H₅₄O₂
• Molecular Weight: 566.868
• Mol file: 70267-38-8.mol

Synonyms:

Chemical Property of 9-Z-(3R,3'R)-diatoxanthin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-Z-(3R,3'R)-diatoxanthin

There total 8 articles about 9-Z-(3R,3'R)-diatoxanthin 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:

<(3R)-3-hydroxy-12'-apo-β-carotenyl>triphenylphosphonium bromide + 2-Z-5-((4'R)-4'-hydroxy-2',2',6'-trimethylcyclohex-1'-enyl)-3-methyl-2-penten-4-yn-1-al (160332-75-2) → 9-Z-(3R,3'R)-diatoxanthin (70267-38-8)

Guidance literature:

With sodium hydride; In dichloromethane; at 20 ℃; for 48h; Yield given;

DOI:10.1016/0957-4166(94)80087-1

Reference yield:

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one (20548-02-1,55058-51-0,60686-81-9,60686-82-0,82977-53-5,90082-06-7,90129-05-8,99881-84-2,60046-50-6) → 9-Z-(3R,3'R)-diatoxanthin (70267-38-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / Et₃N / diethyl ether / 15 h / 0 - 20 °C

2: 1.) EtMgBr / 1.) Et₂O, CH₂Cl₂, reflux, 1 h, 2.) Et₂O, CH₂Cl₂, reflux, 14 h

3: 68 percent / KOH / methanol / 2 h / 20 °C

4: 82 percent / AcOH, KHSO₄ / 1.75 h / 70 °C

5: 94 percent / 5percent methanolic KOH / 1 h / 20 °C

6: 60 percent / MnO₂ / CH₂Cl₂ / 20 h / 20 °C

7: NaH / CH₂Cl₂ / 48 h / 20 °C

With manganese(IV) oxide; potassium hydroxide; potassium hydrogensulfate; ethylmagnesium bromide; sodium hydride; acetic acid; triethylamine; In methanol; diethyl ether; dichloromethane;

DOI:10.1016/0957-4166(94)80087-1

Reference yield:

(R)-4-<(E/Z)-5-hydroxy-3-methylpent-3-en-1-ynyl>-3,5,5-trimethylcyclohex-3-enol (26533-77-7,95307-33-8,95307-42-9,98718-44-6,98718-45-7) → 9-Z-(3R,3'R)-diatoxanthin (70267-38-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / MnO₂ / CH₂Cl₂ / 20 h / 20 °C

2: NaH / CH₂Cl₂ / 48 h / 20 °C

With manganese(IV) oxide; sodium hydride; In dichloromethane;

DOI:10.1016/0957-4166(94)80087-1

upstream raw materials:

2-Z-5-((4'R)-4'-hydroxy-2',2',6'-trimethylcyclohex-1'-enyl)-3-methyl-2-penten-4-yn-1-al

Diadinoxanthinditrimethylsilylether

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one

(R)-4-<(E/Z)-5-hydroxy-3-methylpent-3-en-1-ynyl>-3,5,5-trimethylcyclohex-3-enol