[(E)-(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-7-oxo-oct-5-enyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(E)-(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-7-oxo-oct-5-enyl]-carbamic acid benzyl ester
• CAS No.: 269715-87-9
• Molecular Formula: C₃₀H₅₃NO₅Si₂
• Molecular Weight: 563.926

Synonyms:[(E)-(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-7-oxo-oct-5-enyl]-carbamic acid benzyl ester

Chemical Property of [(E)-(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-7-oxo-oct-5-enyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(E)-(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-7-oxo-oct-5-enyl]-carbamic acid benzyl ester

There total 8 articles about [(E)-(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-7-oxo-oct-5-enyl]-carbamic acid benzyl ester 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: 64.0%

dimethyl (2-oxopropyl)phosphonate (4202-14-6) + [(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-5-oxo-pentyl]-(2,2,2-trifluoro-acetyl)-carbamic acid benzyl ester (269715-86-8) → 4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-3-methyl-piperidine-1-carboxylic acid benzyl ester + [(E)-(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-7-oxo-oct-5-enyl]-carbamic acid benzyl ester (269715-87-9)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(99)02348-5

Reference yield:

3-benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyric acid tert-butyl ester (269715-77-7) → [(E)-(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-7-oxo-oct-5-enyl]-carbamic acid benzyl ester (269715-87-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / DIBAL-H / toluene / -78 °C

2: 51 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

3: 100 percent / 2,6-lutidine

4: 90 percent / Et₃N

5: 91 percent / O₃; PPh₃ / CH₂Cl₂ / -78 °C

6: 64 percent / LDA / tetrahydrofuran

With 2,6-dimethylpyridine; boron trifluoride diethyl etherate; diisobutylaluminium hydride; ozone; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; 1: Reduction / 2: allylation / 3: Etherification / 4: Acylation / 5: ozonolysis / 6: Wittig reaction;

DOI:10.1016/S0040-4039(99)02348-5

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → [(E)-(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-7-oxo-oct-5-enyl]-carbamic acid benzyl ester (269715-87-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / 2,6-lutidine

2: 90 percent / Et₃N

3: 91 percent / O₃; PPh₃ / CH₂Cl₂ / -78 °C

4: 64 percent / LDA / tetrahydrofuran

With 2,6-dimethylpyridine; ozone; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 1: Etherification / 2: Acylation / 3: ozonolysis / 4: Wittig reaction;

DOI:10.1016/S0040-4039(99)02348-5

upstream raw materials:

dimethyl (2-oxopropyl)phosphonate

[(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-5-oxo-pentyl]-(2,2,2-trifluoro-acetyl)-carbamic acid benzyl ester

t-butyldimethylsiyl triflate

[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-3-oxo-propyl]-carbamic acid benzyl ester

Downstream raw materials:

((3R,4aS,6S,7R,8S)-6-Hydroxy-8-hydroxymethyl-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl)-carbamic acid benzyl ester

[6-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl]-carbamic acid benzyl ester

(3R,4aS,6S,7R,8S)-1-[(E)-Benzyloxycarbonylimino]-6-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-hexahydro-pyrido[1,2-c]pyrimidine-2-carboxylic acid benzyl ester

{[(E)-Benzyloxycarbonylimino]-[(2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2-hydroxy-propyl)-3-methyl-piperidin-1-yl]-methyl}-carbamic acid benzyl ester

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