(-)-(E)-1-<(2R,3S)-4-<(tert-Butyldimethylsilyl)oxy>-2,2-(ethylenedioxy)-6-hydroxy-5-methyl-1-hexylidene>-2-formyl-2-cyclohexene

Base Information

• Chemical Name: (-)-(E)-1-<(2R,3S)-4-<(tert-Butyldimethylsilyl)oxy>-2,2-(ethylenedioxy)-6-hydroxy-5-methyl-1-hexylidene>-2-formyl-2-cyclohexene
• CAS No.: 158830-96-7
• Molecular Formula: C₂₂H₃₈O₅Si
• Molecular Weight: 410.626
• Mol file: 158830-96-7.mol

Synonyms:(-)-(E)-1-<(2R,3S)-4-<(tert-Butyldimethylsilyl)oxy>-2,2-(ethylenedioxy)-6-hydroxy-5-methyl-1-hexylidene>-2-formyl-2-cyclohexene

Chemical Property of (-)-(E)-1-<(2R,3S)-4-<(tert-Butyldimethylsilyl)oxy>-2,2-(ethylenedioxy)-6-hydroxy-5-methyl-1-hexylidene>-2-formyl-2-cyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(E)-1-<(2R,3S)-4-<(tert-Butyldimethylsilyl)oxy>-2,2-(ethylenedioxy)-6-hydroxy-5-methyl-1-hexylidene>-2-formyl-2-cyclohexene

There total 10 articles about (-)-(E)-1-<(2R,3S)-4-<(tert-Butyldimethylsilyl)oxy>-2,2-(ethylenedioxy)-6-hydroxy-5-methyl-1-hexylidene>-2-formyl-2-cyclohexene 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: 60.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + (-)-(E)-2-Bromo-1-<(2R,3S)-4-<(tert-butyldimethylsilyl)oxy>-2,2-(ethylenedioxy)-6-hydroxy-5-methyl-1-hexylidene>-2-cyclohexene (160084-57-1) → (-)-(E)-1-<(2R,3S)-4-<(tert-Butyldimethylsilyl)oxy>-2,2-(ethylenedioxy)-6-hydroxy-5-methyl-1-hexylidene>-2-formyl-2-cyclohexene (158830-96-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; 1.) -78 deg C, 1 h, 2.) -78 deg C, 2 h;

DOI:10.1021/jo00098a017

Reference yield:

(E)-2-Bromo-1-<3-carbomethoxy-2-oxo-1-propylidene>-2-cyclohexene (158830-93-4) → (-)-(E)-1-<(2R,3S)-4-<(tert-Butyldimethylsilyl)oxy>-2,2-(ethylenedioxy)-6-hydroxy-5-methyl-1-hexylidene>-2-formyl-2-cyclohexene (158830-96-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / p-TsOH*H₂O / benzene / 36 h / Heating

2: 70 percent / DIBAL-H / toluene; hexane / 0.5 h / -78 °C

4: 79 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5: 83 percent / LiBH₄ / tetrahydrofuran / 240 h / 4 °C

6: 60 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 1 h, 2.) -78 deg C, 2 h

With lithium borohydride; n-butyllithium; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; benzene;

DOI:10.1021/jo00098a017

Reference yield:

(E)-2-Bromo-1-<3-carbomethoxy-2,2-(ethylenedioxy)-1-propylidene>-2-cyclohexene → (-)-(E)-1-<(2R,3S)-4-<(tert-Butyldimethylsilyl)oxy>-2,2-(ethylenedioxy)-6-hydroxy-5-methyl-1-hexylidene>-2-formyl-2-cyclohexene (158830-96-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / DIBAL-H / toluene; hexane / 0.5 h / -78 °C

3: 79 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4: 83 percent / LiBH₄ / tetrahydrofuran / 240 h / 4 °C

5: 60 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 1 h, 2.) -78 deg C, 2 h

With lithium borohydride; n-butyllithium; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1021/jo00098a017

upstream raw materials:

N,N-dimethyl-formamide

(-)-(E)-2-Bromo-1-<(2R,3S)-4-<(tert-butyldimethylsilyl)oxy>-2,2-(ethylenedioxy)-6-hydroxy-5-methyl-1-hexylidene>-2-cyclohexene

t-butyldimethylsiyl triflate

(E)-2-Bromo-1-<3-carbomethoxy-2-oxo-1-propylidene>-2-cyclohexene