Benzo(3,4)furo(3',4':6,7)cycloocta(1,2-f)(1,3)benzodioxol-3(1H)-one, 3a,4,14,14a-tetrahydro-14-(acetyloxy)-6,7,8-trimethoxy-, stereoisomer

Base Information

• Chemical Name: Benzo(3,4)furo(3',4':6,7)cycloocta(1,2-f)(1,3)benzodioxol-3(1H)-one, 3a,4,14,14a-tetrahydro-14-(acetyloxy)-6,7,8-trimethoxy-, stereoisomer
• CAS No.: 41451-68-7
• Molecular Formula: C24H24O9
• Molecular Weight: 456.445
• Mol file: 41451-68-7.mol

Synonyms:Benzo(3,4)furo(3',4':6,7)cycloocta(1,2-f)(1,3)benzodioxol-3(1H)-one, 3a,4,14,14a-tetrahydro-14-(acetyloxy)-6,7,8-trimethoxy-, stereoisomer;LS-35400

Chemical Property of Benzo(3,4)furo(3',4':6,7)cycloocta(1,2-f)(1,3)benzodioxol-3(1H)-one, 3a,4,14,14a-tetrahydro-14-(acetyloxy)-6,7,8-trimethoxy-, stereoisomer

Chemical Property:

• XLogP3: -0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 456.14203234
• Heavy Atom Count: 33
• Complexity: 1060

Purity/Quality:

99% ^*data from raw suppliers

STEGANACIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC1C2C(C(C(C2=CC3=CC4C(C=CC=C13)C(=O)C(=O)C(=O)C4=O)OC)OC)OC
• Isomeric SMILES: CC(=O)OC\1C2C(C(C(C2=C/C/3=C/C4C(/C=C/C=C13)C(=O)C(=O)C(=O)C4=O)OC)OC)OC

Technology Process of Benzo(3,4)furo(3',4':6,7)cycloocta(1,2-f)(1,3)benzodioxol-3(1H)-one, 3a,4,14,14a-tetrahydro-14-(acetyloxy)-6,7,8-trimethoxy-, stereoisomer

There total 68 articles about Benzo(3,4)furo(3',4':6,7)cycloocta(1,2-f)(1,3)benzodioxol-3(1H)-one, 3a,4,14,14a-tetrahydro-14-(acetyloxy)-6,7,8-trimethoxy-, stereoisomer 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:

2-<1'-(2'-bromo-4',5'-methylenedioxyphenyl)>-2-methyl-1,3-oxathiolane (73252-66-1) → (+/-)-steganacin (41451-68-7,58894-52-3,61176-82-7,69428-65-5,69609-67-2,69979-99-3,76250-30-1,107493-08-3,107493-09-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) n-BuLi, 2.) CuI*P(OEt)3

2: 15percent aq. AcOH / 12 h

3: 78 percent / piperidine / benzene / 10 h / Heating

4: 91 percent / methyl iodide, H₂O / acetone / 12 h / Heating

5: 95 percent / hydrogen / Ni(R) W-2 / ethanol / atmospheric pressure

6: 85 percent / pyridinium hydrobromide perbromide, CF₃COOH / CH₂Cl₂ / 3.5 h / 25 °C

7: 73 percent / t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 1.5 h / 25 °C

8: 220 mg / 2.7 M KOH / ethanol / 10 h / Heating

9: 0.17 h / 200 °C

10: 1.) H₂O, KOH, 2.) Jones reagent

11: NaBH₄

12: acetylation

With piperidine; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; jones reagent; triethylphosphite copper(I) iodide complex; potassium tert-butylate; water; hydrogen; pyridinium hydrobromide perbromide; acetic acid; trifluoroacetic acid; methyl iodide; Ni(R) W-2; In tetrahydrofuran; ethanol; dichloromethane; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/ja00522a058

Reference yield:

2-<2''-(2''-methyl-1'',3''-oxathiolane)>-4,5-methylenedioxy-4',5',6'-trimethoxy-1,1'-biphenyl-2'-carboxaldehyde (69138-98-3,69177-15-7,73285-71-9) → (+/-)-steganacin (41451-68-7,58894-52-3,61176-82-7,69428-65-5,69609-67-2,69979-99-3,76250-30-1,107493-08-3,107493-09-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 78 percent / piperidine / benzene / 10 h / Heating

2: 91 percent / methyl iodide, H₂O / acetone / 12 h / Heating

3: 95 percent / hydrogen / Ni(R) W-2 / ethanol / atmospheric pressure

4: 85 percent / pyridinium hydrobromide perbromide, CF₃COOH / CH₂Cl₂ / 3.5 h / 25 °C

5: 73 percent / t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 1.5 h / 25 °C

6: 220 mg / 2.7 M KOH / ethanol / 10 h / Heating

7: 0.17 h / 200 °C

8: 1.) H₂O, KOH, 2.) Jones reagent

9: NaBH₄

10: acetylation

With piperidine; potassium hydroxide; sodium tetrahydroborate; jones reagent; potassium tert-butylate; water; hydrogen; pyridinium hydrobromide perbromide; trifluoroacetic acid; methyl iodide; Ni(R) W-2; In tetrahydrofuran; ethanol; dichloromethane; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/ja00522a058

Reference yield:

dimethyl 2-<2''-(2''-methyl-1'',3''-oxathiolane)>-4,5-methylenedioxy-4',5',6'-trimethoxy-1,1'-biphenyl-2'-β-methylenemalonate (69138-99-4) → (+/-)-steganacin (41451-68-7,58894-52-3,61176-82-7,69428-65-5,69609-67-2,69979-99-3,76250-30-1,107493-08-3,107493-09-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 91 percent / methyl iodide, H₂O / acetone / 12 h / Heating

2: 95 percent / hydrogen / Ni(R) W-2 / ethanol / atmospheric pressure

3: 85 percent / pyridinium hydrobromide perbromide, CF₃COOH / CH₂Cl₂ / 3.5 h / 25 °C

4: 73 percent / t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 1.5 h / 25 °C

5: 220 mg / 2.7 M KOH / ethanol / 10 h / Heating

6: 0.17 h / 200 °C

7: 1.) H₂O, KOH, 2.) Jones reagent

8: NaBH₄

9: acetylation

With potassium hydroxide; sodium tetrahydroborate; jones reagent; potassium tert-butylate; water; hydrogen; pyridinium hydrobromide perbromide; trifluoroacetic acid; methyl iodide; Ni(R) W-2; In tetrahydrofuran; ethanol; dichloromethane; acetone; tert-butyl alcohol;

DOI:10.1021/ja00522a058

upstream raw materials:

(-)-isostegane

acetic acid

2-(3,4,5-trimethoxyphenyl)-1,3-dithiane

3,4-Methylenedioxybenzyl bromide

Downstream raw materials:

(+/-)-isostegane

(-)-episteganacin

Refernces

Diversity oriented microwave-assisted synthesis of (-)-steganacin aza-analogues

10.1021/jo801290j

The research aims to develop a novel and efficient microwave-assisted protocol for synthesizing aza-analogues of (-)-Steganacin, a naturally occurring bisbenzocyclooctadiene lignan lactone with potent antileukemic and tubulin polymerization inhibitory activity. The study focuses on creating a small library of diversely functionalized aza-analogues to identify their potential antileukemic and tubulin polymerization inhibitory activities. The key steps in the synthesis include the Suzuki-Miyaura cross-coupling reaction to generate the biaryl axis, the A3-coupling reaction to introduce additional diversity, and the intramolecular Huisgen 1,3-dipolar cycloaddition for ring closure. The researchers used various chemicals such as benzyl alcohols, NBS for bromination, TBS-Cl for protection, and different boronic acids for the Suzuki-Miyaura reaction. The A3-coupling involved aldehydes, amines, and alkynes, with CuBr as a catalyst. The final cyclization step utilized Appel bromination, azide displacement, and microwave-assisted Huisgen cycloaddition. The study concluded that the microwave-assisted synthesis resulted in faster and cleaner reactions, yielding the target aza-analogues in high overall yields and purity. The cyclization process exhibited exclusive diastereoselectivity, forming only the 13-(S)-isomer of the target molecules, which was confirmed by NMR analysis and X-ray crystallography. The synthesized compounds are currently being investigated for their biological activities.