(6aS,12aS,5'S)-5'-(phenylseleno)dihydrodeguelin

Base Information

• Chemical Name: (6aS,12aS,5'S)-5'-(phenylseleno)dihydrodeguelin
• CAS No.: 70145-45-8
• Molecular Formula: C₂₉H₂₈O₆Se
• Molecular Weight: 551.498
• Mol file: 70145-45-8.mol

Synonyms:(6aS,12aS,5'S)-5'-(phenylseleno)dihydrodeguelin

Chemical Property of (6aS,12aS,5'S)-5'-(phenylseleno)dihydrodeguelin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6aS,12aS,5'S)-5'-(phenylseleno)dihydrodeguelin

There total 3 articles about (6aS,12aS,5'S)-5'-(phenylseleno)dihydrodeguelin 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: 42.0%

Phenylselenyl chloride (5707-04-0) + rotenonic acid (70191-71-8) → (6aS,12aS,5'R)-5'-(phenylseleno)dihydrodeguelin (70191-72-9) + (6aS,12aS,5'S)-5'-(phenylseleno)dihydrodeguelin (70145-45-8)

Guidance literature:

In dichloromethane; 1) -30 deg C to r.t., 1 h, 2) r.t., 2 h;

Reference yield:

(6aS,12S,12aR)-2,3-Dimethoxy-8-(3-methyl-but-2-enyl)-6,6a,12,12a-tetrahydro-chromeno[3,4-b]chromene-9,12-diol (124571-94-4) → (6aS,12aS,5'S)-5'-(phenylseleno)dihydrodeguelin (70145-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

2: 42 percent / CH₂Cl₂ / 1) -30 deg C to r.t., 1 h, 2) r.t., 2 h

With Dess-Martin periodane; In dichloromethane;

Reference yield:

(6aS,12S,12aS,5'S)-12-deoxo-12-hydroxy-5'-phenylthio-4',5'-dihydrodeguelin (124571-93-3) → (6aS,12aS,5'S)-5'-(phenylseleno)dihydrodeguelin (70145-45-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / potassium naphthalenide / tetrahydrofuran / 0.12 h / -40 °C

2: 40 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

3: 42 percent / CH₂Cl₂ / 1) -30 deg C to r.t., 1 h, 2) r.t., 2 h

With potassium naphthalenide; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

upstream raw materials:

Phenylselenyl chloride

rotenonic acid

(6aS,12S,12aR)-2,3-Dimethoxy-8-(3-methyl-but-2-enyl)-6,6a,12,12a-tetrahydro-chromeno[3,4-b]chromene-9,12-diol

(6aS,12S,12aS,5'S)-12-deoxo-12-hydroxy-5'-phenylthio-4',5'-dihydrodeguelin

Downstream raw materials:

(-)-deguelin

Refernces