sesaminone

Base Information

• Chemical Name: sesaminone
• CAS No.: 157207-93-7
• Molecular Formula: C₂₀H₁₈O₇
• Molecular Weight: 370.359
• Mol file: 157207-93-7.mol

Synonyms:Methanone,1,3-benzodioxol-5-yl[5-(1,3-benzodioxol-5-yl)tetrahydro-4-(hydroxymethyl)-3-furanyl]-,[3S-(3a,4b,5a)]-; Sesaminone

Chemical Property of sesaminone

Chemical Property:

• Vapor Pressure: 2.29E-14mmHg at 25°C
• Melting Point: 133-134 °C
• Boiling Point: 581.6°Cat760mmHg
• PKA: 14.81±0.10(Predicted)
• Flash Point: 211.4°C
• PSA: 83.45000
• Density: 1.414g/cm³
• LogP: 2.32290

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of sesaminone

There total 19 articles about sesaminone 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: 84.0%

Benzo[1,3]dioxol-5-yl-[(3S,4R,5S)-5-benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-methanone (195321-33-6) → sesaminone (157207-93-7)

Guidance literature:

With pyridine; hydrogen fluoride; In acetonitrile; at 0 - 20 ℃; for 24h;

DOI:10.1021/jo971027c

Reference yield: 82.0%

Benzo[1,3]dioxol-5-yl-((3S,4R,5S)-5-benzo[1,3]dioxol-5-yl-4-benzyloxymethyl-tetrahydro-furan-3-yl)-methanone → sesaminone (157207-93-7)

Guidance literature:

With formic acid; palladium;

DOI:10.1055/s-2001-11419

Reference yield: 29.0%

(3,4-methylenedioxy)phenylmagnesium bromide (17680-04-5) + pluviatide (108645-28-9) → (+)-epi-sesaminone (157207-93-7)

Guidance literature:

In tetrahydrofuran; for 12h;

DOI:10.1021/np9702953

upstream raw materials:

Benzo[1,3]dioxol-5-yl-[(3S,4R,5S)-5-benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-methanone

Benzo[1,3]dioxol-5-yl-((3S,4R,5S)-5-benzo[1,3]dioxol-5-yl-4-benzyloxymethyl-tetrahydro-furan-3-yl)-methanol

Acetic acid benzo[1,3]dioxol-5-yl-((3S,4R,5S)-5-benzo[1,3]dioxol-5-yl-4-benzyloxymethyl-tetrahydro-furan-3-yl)-methyl ester

1,2-(methylenedioxy)-4-bromobenzene

Refernces

• 1、 Maioli, Andrew T.,Civiello, Rita L.,Foxman, Bruce M.,Gordon, Dana M.. "Asymmetric synthesis of sesaminone: Confirmation of its structure and determination of its absolute configuration". . p. 7413 - 7417. Retrieved 2007/10/03.