Samin

Base Information

• Chemical Name: Samin
• CAS No.: 166239-82-3
• Molecular Formula: C₁₃H₁₄O₅
• Molecular Weight: 250.251
• UNII: ZI28B199I3
• Nikkaji Number: J732.621A
• Wikidata: Q27295548
• Mol file: 166239-82-3.mol

Synonyms:Samin;(+)-Samin;UNII-ZI28B199I3;ZI28B199I3;166239-82-3;1H,3H-Furo(3,4-C)furan-1-ol, 4-(1,3-benzodioxol-5-yl)tetrahydro-, (1S,3aR,4S,6aR)-;1H,3H-Furo(3,4-C)furan-1-ol, 4-(1,3-benzodioxol-5-yl)tetrahydro-, (1S-(1alpha,3aalpha,4alpha,6aalpha))-;CHEBI:174293;Q27295548;(3S,3aR,6S,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrouro[3,4-c]uran-6-ol;1H,3H-FURO(3,4-C)FURAN-1-OL, 4-(1,3-BENZODIOXOL-5-YL)TETRAHYDRO-, (1S-(1.ALPHA.,3A.ALPHA.,4.ALPHA.,6A.ALPHA.))-

Chemical Property of Samin

Chemical Property:

• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 250.08412354
• Heavy Atom Count: 18
• Complexity: 323

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C2C(COC2O)C(O1)C3=CC4=C(C=C3)OCO4
• Isomeric SMILES: C1[C@H]2[C@H](CO[C@@H]2O)[C@H](O1)C3=CC4=C(C=C3)OCO4

Technology Process of Samin

There total 2 articles about Samin 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: 95.0%

sesamolin (526-07-8,18709-03-0,116562-16-4) → (+)-samin (166239-82-3)

Guidance literature:

With Amberlyst-15; In water; acetonitrile; at 70 ℃; for 5h;

DOI:10.1080/14786419.2018.1553169

Reference yield:

sesamolin (526-07-8,18709-03-0,116562-16-4) → (+)-disaminyl ether (30186-93-7) + (+)-samin (166239-82-3)

Guidance literature:

With sulfuric acid; In ethanol;

DOI:10.1021/np9702953

Reference yield: 80.0%

4-benzyloxy-3-methoxyphenol (40232-88-0) + (+)-samin (166239-82-3) → 5-[(1S,3aR,4S,6aR)-4-(4-Benzyloxy-3-methoxy-phenoxy)-tetrahydro-furo[3,4-c]furan-1-yl]-benzo[1,3]dioxole

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1139/v97-102

upstream raw materials:

sesamolin

Downstream raw materials:

(+)-epi-sesaminone

4-((1S,3aR,4S,6aR)-4-Benzo[1,3]dioxol-5-yl-tetrahydro-furo[3,4-c]furan-1-yloxy)-2-methoxy-phenol

Refernces

• 1、 Worawalai, Wisuttaya,Khongchai, Phonpimon,Surachaitanawat, Nantaporn,Phuwapraisirisan, Preecha. "Synthesis of furofuran lignans as antidiabetic agents simultaneously achieved by inhibiting α-glucosidase and free radical". . p. 1370 - 1381. Retrieved 2016.
• 2、 Marchand, Patrice A.,Zajicek, Jaroslav,Lewis, Norman G.. "Oxygen insertion in Sesamum indicum furanofuran lignans. Diastereoselective syntheses of enzyme substrate analogues". . p. 840 - 849. Retrieved 2007/10/03.