1,4-Butanediol, 2,3-bis(1,3-benzodioxol-5-ylmethyl)-, diacetate, (2R,3R)-

Base Information

• Chemical Name: 1,4-Butanediol, 2,3-bis(1,3-benzodioxol-5-ylmethyl)-, diacetate, (2R,3R)-
• CAS No.: 81410-43-7
• Molecular Formula: C₂₄H₂₆O₈
• Molecular Weight: 442.466
• DSSTox Substance ID: DTXSID001001974
• Nikkaji Number: J2.166.584C
• Metabolomics Workbench ID: 132344
• ChEMBL ID: CHEMBL3582086
• Mol file: 81410-43-7.mol

Synonyms:81410-43-7;CHEMBL3582086;DTXSID001001974;1,4-Butanediol, 2,3-bis(1,3-benzodioxol-5-ylmethyl)-, diacetate, (2R,3R)-;(2R,3R)-2,3-Bis[(1,3-benzodioxole-5-yl)methyl]-1,4-butanediol diacetate;2,3-Bis[(2H-1,3-benzodioxol-5-yl)methyl]butane-1,4-diyl diacetate

Chemical Property of 1,4-Butanediol, 2,3-bis(1,3-benzodioxol-5-ylmethyl)-, diacetate, (2R,3R)-

Chemical Property:

• Vapor Pressure: 4.24E-14mmHg at 25°C
• Boiling Point: 594.4°C at 760 mmHg
• Flash Point: 256.5°C
• Density: 1.282g/cm³
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 442.16276778
• Heavy Atom Count: 32
• Complexity: 586

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(CC1=CC2=C(C=C1)OCO2)C(CC3=CC4=C(C=C3)OCO4)COC(=O)C
• Isomeric SMILES: CC(=O)OC[C@H](CC1=CC2=C(C=C1)OCO2)[C@@H](CC3=CC4=C(C=C3)OCO4)COC(=O)C

Technology Process of 1,4-Butanediol, 2,3-bis(1,3-benzodioxol-5-ylmethyl)-, diacetate, (2R,3R)-

There total 9 articles about 1,4-Butanediol, 2,3-bis(1,3-benzodioxol-5-ylmethyl)-, diacetate, (2R,3R)- 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: 92.0%

acetic anhydride (108-24-7) + (-)-dihydrocubebin (24563-03-9) → ariensin (81410-43-7)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃;

DOI:10.3184/030823409X12506792542747

Reference yield:

piperonal (120-57-0,30024-74-9) → ariensin (81410-43-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / -30 °C

1.2: 97 percent / tetrahydrofuran / 0.5 h / -30 °C

2.1: 90 percent / hydrogen; AcOH / Pd(OH)2/C / tetrahydrofuran / 20 °C / 760 Torr

3.1: 97 percent / lithium aluminum hydride / tetrahydrofuran / 1.5 h / 0 - 20 °C

4.1: Candida rugosa lipase AY / 72 h / 20 °C

With lithium aluminium tetrahydride; Candida rugosa lipase AY; hydrogen; acetic acid; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran;

DOI:10.1081/SCC-200051037

Reference yield:

4-(1,3-benzodioxol-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one (80483-34-7) → ariensin (81410-43-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / -30 °C

1.2: 97 percent / tetrahydrofuran / 0.5 h / -30 °C

2.1: 90 percent / hydrogen; AcOH / Pd(OH)2/C / tetrahydrofuran / 20 °C / 760 Torr

3.1: 97 percent / lithium aluminum hydride / tetrahydrofuran / 1.5 h / 0 - 20 °C

4.1: Candida rugosa lipase AY / 72 h / 20 °C

With lithium aluminium tetrahydride; Candida rugosa lipase AY; hydrogen; acetic acid; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran;

DOI:10.1081/SCC-200051037

upstream raw materials:

acetic anhydride

threo-(-)-2,3-bis(3',4'-methylenedioxybenzyl)-1,4-butanediol monoacetate

(-)-dihydrocubebin

vinyl acetate