InteriotherinA

Base Information

• Chemical Name: InteriotherinA
• CAS No.: 181701-06-4
• Molecular Formula: C29H28O8
• Molecular Weight: 504.5278
• DSSTox Substance ID: DTXSID701317033
• Wikidata: Q105160737
• Mol file: 181701-06-4.mol

Synonyms:InteriotherinA;181701-06-4;Interiotherins A;(3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.02,10.04,8.017,21]docosa-1(22),2,4(8),9,15,17(21)-hexaen-11-yl) benzoate;(-)-Interiotherin A;Cycloocta(1,2-f:3,4-f')bis(1,3)benzodioxol-5-ol, 5,6,7,8-tetrahydro-13,14-dimethoxy-6,7-dimethyl-, benzoate, (5R,6S,7S,13aS)-;Cycloocta(1,2-f:3,4-f')bis(1,3)benzodioxol-5-ol, 5,6,7,8-tetrahydro-13,14-dimethoxy-6,7-dimethyl-, benzoate, stereoisomer;DTXSID701317033;HY-N6849;AKOS040760466;CS-0100270

Chemical Property of InteriotherinA

Chemical Property:

• XLogP3: 6.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 504.17841785
• Heavy Atom Count: 37
• Complexity: 801

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2=CC3=C(C(=C2C4=C(C5=C(C=C4C(C1C)OC(=O)C6=CC=CC=C6)OCO5)OC)OC)OCO3

Technology Process of InteriotherinA

There total 17 articles about InteriotherinA 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: 62.0%

kadsuphilin B + benzoic acid (65-85-0,8013-63-6) → interiotherin A (181701-06-4)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 25 ℃; for 10h;

DOI:10.1021/ol050476t

Reference yield:

3-Hydroxy-4,5-(methylenedioxy)benzaldehyde (81805-98-3) → interiotherin A (181701-06-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 97 percent / N-bromosuccinimide / dioxane / 12 h / 15 - 19 °C

2.1: 85 percent / K₂CO₃ / acetone / 2 h / 56 °C

3.1: 75 percent / CH₂Cl₂ / -50 - 0 °C

4.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / -78 °C

5.1: tetrahydrofuran / 0 - 25 °C

6.1: 0.29 g / Pd(PPh₃)4; Ph₃P; NaOH / tetrahydrofuran; H₂O / 22 h / 70 °C

7.1: 98 percent / H₂ / Pd/C / ethyl acetate / 6 h / 20 °C

8.1: 90 percent / N-bromosuccinimide / dioxane / 11 h / 15 - 19 °C

9.1: 95 percent / K₂CO₃ / acetone / 2 h / 56 °C

10.1: t-BuLi / various solvent(s) / 0.25 h / -78 °C

10.2: CuCN / various solvent(s) / 2.5 h / -78 - -40 °C

10.3: 69 percent / 1,3-dinitrobenzene / various solvent(s) / 10 h / 25 °C

11.1: 89 percent / n-Bu₄NF / tetrahydrofuran / 12 h / 55 °C

12.1: 62 percent / Ph₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 10 h / 25 °C

With 2,6-dimethylpyridine; sodium hydroxide; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; potassium carbonate; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; acetone; 6.1: Suzuki-Miyaura reaction / 12.1: Mitsunobu inversion;

DOI:10.1021/jo051525i

Reference yield:

6-bromo-7-methoxybenzo[d][1,3] dioxole-5-carbaldehyde (795278-07-8) → interiotherin A (181701-06-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 75 percent / CH₂Cl₂ / -50 - 0 °C

2.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / -78 °C

3.1: tetrahydrofuran / 0 - 25 °C

4.1: 0.29 g / Pd(PPh₃)4; Ph₃P; NaOH / tetrahydrofuran; H₂O / 22 h / 70 °C

5.1: 98 percent / H₂ / Pd/C / ethyl acetate / 6 h / 20 °C

6.1: 90 percent / N-bromosuccinimide / dioxane / 11 h / 15 - 19 °C

7.1: 95 percent / K₂CO₃ / acetone / 2 h / 56 °C

8.1: t-BuLi / various solvent(s) / 0.25 h / -78 °C

8.2: CuCN / various solvent(s) / 2.5 h / -78 - -40 °C

8.3: 69 percent / 1,3-dinitrobenzene / various solvent(s) / 10 h / 25 °C

9.1: 89 percent / n-Bu₄NF / tetrahydrofuran / 12 h / 55 °C

10.1: 62 percent / Ph₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 10 h / 25 °C

With 2,6-dimethylpyridine; sodium hydroxide; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; potassium carbonate; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; acetone; 4.1: Suzuki-Miyaura reaction / 10.1: Mitsunobu inversion;

DOI:10.1021/jo051525i

upstream raw materials:

benzoic acid

(1S,2S)-1-(5-bromo-4-methoxybenzo[d][1,3]dioxol-6-yl)-2,3-dimethylbut-3-en-1-ol

((1S,2S)-1-(5-bromo-4-methoxybenzo[d][1,3]dioxol-6-yl)-2,3-dimethylbut-3-enyloxy)(tert-butyl)dimethylsilane

((1S,2S,3S)-4-(4-hydroxybenzo[d][1,3]dioxol-6-yl)-1-(5-bromo-4-methoxybenzo[d][1,3]dioxol-6-yl)-2,3-dimethylbutoxy)(tert-butyl)dimethylsilane

Refernces

• 1、 Coleman, Robert S.,Gurrala, Srinivas Reddy,Mitra, Soumya,Raao, Amresh. "Asymmetric total synthesis of dibenzocyclooctadiene lignan natural products". . p. 8932 - 8941. Retrieved 2007/10/03.