(4S,5R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(E)-(1R,6R)-6-(tert-butyl-diphenyl-silanyloxy)-1,3,7-trimethyl-2-oxo-oct-3-enyl]-5-methyl-oxocan-2-one

Base Information

• Chemical Name: (4S,5R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(E)-(1R,6R)-6-(tert-butyl-diphenyl-silanyloxy)-1,3,7-trimethyl-2-oxo-oct-3-enyl]-5-methyl-oxocan-2-one
• CAS No.: 161029-82-9
• Molecular Formula: C₄₁H₆₄O₅Si₂
• Molecular Weight: 693.127

Synonyms:(4S,5R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(E)-(1R,6R)-6-(tert-butyl-diphenyl-silanyloxy)-1,3,7-trimethyl-2-oxo-oct-3-enyl]-5-methyl-oxocan-2-one

Chemical Property of (4S,5R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(E)-(1R,6R)-6-(tert-butyl-diphenyl-silanyloxy)-1,3,7-trimethyl-2-oxo-oct-3-enyl]-5-methyl-oxocan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (4S,5R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(E)-(1R,6R)-6-(tert-butyl-diphenyl-silanyloxy)-1,3,7-trimethyl-2-oxo-oct-3-enyl]-5-methyl-oxocan-2-one

There total 18 articles about (4S,5R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(E)-(1R,6R)-6-(tert-butyl-diphenyl-silanyloxy)-1,3,7-trimethyl-2-oxo-oct-3-enyl]-5-methyl-oxocan-2-one 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:

(4S,5R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(E)-(1S,6R)-6-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-1,3,7-trimethyl-oct-3-enyl]-5-methyl-oxocan-2-one → (4S,5R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(E)-(1R,6R)-6-(tert-butyl-diphenyl-silanyloxy)-1,3,7-trimethyl-2-oxo-oct-3-enyl]-5-methyl-oxocan-2-one (161029-82-9)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 0.666667h; Yield given; Ambient temperature;

DOI:10.1021/ja00097a060

Reference yield:

(S)-3-methylbutane-1,2-diol (24347-56-6) → (4S,5R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(E)-(1R,6R)-6-(tert-butyl-diphenyl-silanyloxy)-1,3,7-trimethyl-2-oxo-oct-3-enyl]-5-methyl-oxocan-2-one (161029-82-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) MsCl, Et₃N, 2.) K₂CO₃, MeOH, 3.) BF₃*Et₂O

2: 83 percent / imidazole / dimethylformamide / Ambient temperature

3: 1.) dicyclohexylborane, 2.) MeLi / 1.) THF, from 0 to RT, overnight, 2.) THF, from 0 to RT, 50.5 h

4: Br₂ / CH₂Cl₂ / 0.08 h / -78 °C

5: MeONa / CH₂Cl₂; methanol / 1.) 0 deg C, 1 h, 2.) RT, 2 h

6: 1.) tBuLi / 1.) THF, Et₂O, -100 deg C, 2.) THF, Et₂O, 10 min

7: periodinane / CH₂Cl₂ / 0.67 h / Ambient temperature

With 1H-imidazole; methanol; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; methyllithium; bromine; tert.-butyl lithium; sodium methylate; potassium carbonate; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00097a060

Reference yield:

(S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) → (4S,5R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(E)-(1R,6R)-6-(tert-butyl-diphenyl-silanyloxy)-1,3,7-trimethyl-2-oxo-oct-3-enyl]-5-methyl-oxocan-2-one (161029-82-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 97 percent / LiAlH₄ / tetrahydrofuran / 7 h / Heating

2: 1.) MsCl, Et₃N, 2.) K₂CO₃, MeOH, 3.) BF₃*Et₂O

3: 83 percent / imidazole / dimethylformamide / Ambient temperature

4: 1.) dicyclohexylborane, 2.) MeLi / 1.) THF, from 0 to RT, overnight, 2.) THF, from 0 to RT, 50.5 h

5: Br₂ / CH₂Cl₂ / 0.08 h / -78 °C

6: MeONa / CH₂Cl₂; methanol / 1.) 0 deg C, 1 h, 2.) RT, 2 h

7: 1.) tBuLi / 1.) THF, Et₂O, -100 deg C, 2.) THF, Et₂O, 10 min

8: periodinane / CH₂Cl₂ / 0.67 h / Ambient temperature

With 1H-imidazole; methanol; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; methyllithium; bromine; tert.-butyl lithium; sodium methylate; potassium carbonate; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00097a060

upstream raw materials:

(S)-3-methylbutane-1,2-diol

(S)-2-Hydroxy-3-methylbutanoic acid

Chloro-acetic acid (R)-2-((1R,4S,5R)-4-hydroxy-5-methyl-2-oxo-cycloheptyl)-propyl ester

(4S,5R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-((S)-2-hydroxy-1-methyl-ethyl)-5-methyl-oxocan-2-one

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