Bretonin B

Base Information

• Chemical Name: Bretonin B
• CAS No.: 137623-93-9
• Molecular Formula: C₂₂H₃₀O₅
• Molecular Weight: 374.477
• Mol file: 137623-93-9.mol

Synonyms:

Chemical Property of Bretonin B

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bretonin B

There total 25 articles about Bretonin B 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: 90.0%

(1R)-2-(((4E,8E)-6-((tert-butyl(dimethyl)silyl)oxy)-7-(triethylsilyl)dodeca-4,8-dien-1-yl)oxy)-1-(((tert-butyl(diphenyl)silyl)oxy)methyl)ethyl 4-(tert-butyl(diphenyl)silyloxy)benzoate → (+)-bretonin B (137623-93-9)

Guidance literature:

With pyridine; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/c2cc36604e DOI:10.1039/c2cc36604e

Reference yield: 75.0%

(R)-1-((tert-butyldiphenylsilyl)oxy)-3-(((4E,6Z,8E)-dodeca-4,6,8-trien-1-yl)oxy)propan-2-yl 4-((tert-butyldiphenylsilyl)-oxy)benzoate → (+)-bretonin B (137623-93-9)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 2h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.joc.0c00446

Reference yield:

(S)-3-(4-(4-methoxybenzyloxy)butoxy)propan-1,2-diol (1415037-55-6) → (+)-bretonin B (137623-93-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C

2.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 3 h / 0 - 20 °C / pH 7

4.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 0 - 20 °C

6.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.05 h / -78 °C / Inert atmosphere

6.2: 1 h / -78 °C / Inert atmosphere

7.1: pyridine; / tetrahydrofuran / 20 °C

With pyridine; 1H-imidazole; di-isopropyl azodicarboxylate; potassium hexamethylsilazane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 2.1: |Mitsunobu Displacement / 4.1: |Mitsunobu Displacement / 6.2: |Julia-Kocienski Olefination;

DOI:10.1039/c2cc36604e DOI:10.1039/c2cc36604e

upstream raw materials:

(S)-3-(4-(4-methoxybenzyloxy)butoxy)propan-1,2-diol

(S)-1-(4-methoxyphenyl)-13,13-dimethyl-12,12-diphenyl-2,7,11-trioxa-12-silatetradecan-9-ol

4-hydroxy-benzaldehyde

4-(tert-butyldiphenylsilyloxy)benzaldehyde

Downstream raw materials:

(R)-2-(acetyloxy)-1-{[(4E,6Z,8E)-dodeca-4,6,8-trien-1-yloxy]methyl}ethyl 4-(acetyloxy)benzoate