Diasesamin

Base Information

• Chemical Name: Diasesamin
• CAS No.: 551-30-4
• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.359
• Mol file: 551-30-4.mol

Synonyms:Diasesamin

Chemical Property of Diasesamin

Chemical Property:

Purity/Quality:

99% (HPLC) ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Diasesamin

There total 167 articles about Diasesamin 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: 96.0%

(1S,3aR,4S,6aR)-1,4-bis(6-bromobenzo[d][1,3]dioxol-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan → sesamin (133-03-9,133-04-0,133-05-1,551-30-4,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9,607-80-7)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium formate; In N,N-dimethyl-formamide; at 80 ℃; for 12h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

DOI:10.1016/j.tet.2020.131483

Reference yield: 60.0%

4,8-dihydroxysesamin (63398-39-0) → sesamin (133-03-9,133-04-0,133-05-1,551-30-4,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9,607-80-7)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/j.tetasy.2005.11.007

Reference yield: 12.0%

(3,4-methylenedioxy)phenylmagnesium bromide (17680-04-5) + (+)-samin (166239-82-3) → sesamin (133-03-9,133-04-0,133-05-1,551-30-4,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9,607-80-7) + episesamin (133-04-0,133-05-1,551-30-4,607-80-7,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9,133-03-9)

Guidance literature:

(3,4-methylenedioxy)phenylmagnesium bromide; (+)-samin; In tetrahydrofuran; at 40 ℃; Inert atmosphere;

With pyridine; methanesulfonyl chloride; In tetrahydrofuran; dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1039/d0cc05640e

upstream raw materials:

sesamin

ethylene glycol

(3,4-methylenedioxy)phenylmagnesium bromide

Downstream raw materials:

sesamin

(-)-dihydrocubebin

2-endo,6-endo-bis(3',4'-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane

rac-(1R,2R,5R,6S)-2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane

Refernces

• 1、 Zhao, Can,Khan, Ijaz,Zhang, Yong Jian. "Enantioselective total synthesis of furofuran lignans via Pd-catalyzed asymmetric allylic cycloadditon of vinylethylene carbonates with 2-nitroacrylates". supporting information. p. 12431 - 12434. Retrieved 2020/10/30.
• 2、 Mori, Naoki,Furuta, Akiko,Watanabe, Hidenori. "Electochemical asymmetric dimerization of cinnamic acid derivatives and application to the enantioselective syntheses of furofuran lignans". . p. 8393 - 8399. Retrieved 2016/12/06.