5-[(1S,3aS,5R,6S,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-1-(dimethyl-phenyl-silanyl)-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid methyl ester

Base Information

• Chemical Name: 5-[(1S,3aS,5R,6S,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-1-(dimethyl-phenyl-silanyl)-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid methyl ester
• CAS No.: 127744-14-3
• Molecular Formula: C₂₉H₄₅NO₃Si₂
• Molecular Weight: 511.852
• Mol file: 127744-14-3.mol

Synonyms:

Chemical Property of 5-[(1S,3aS,5R,6S,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-1-(dimethyl-phenyl-silanyl)-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(1S,3aS,5R,6S,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-1-(dimethyl-phenyl-silanyl)-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid methyl ester

There total 10 articles about 5-[(1S,3aS,5R,6S,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-1-(dimethyl-phenyl-silanyl)-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid methyl 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: 6.0%

5-[(1S,3aR,5S,6R,6aR)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-6-cyano-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid methyl ester (127744-11-0,127744-12-1) → 5-[(1S,3aS,5R,6S,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-1-(dimethyl-phenyl-silanyl)-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid methyl ester (127744-14-3) + (R)-5-[(3aR,4S,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-4-cyano-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-5-(dimethyl-phenyl-silanyl)-pentanoic acid methyl ester (127744-13-2,127744-15-4)

Guidance literature:

In tetrahydrofuran; diethyl ether; pentane; at 0 ℃; for 2h;

DOI:10.1039/a804274h

Reference yield:

methyl 4-formylbutanoate (6026-86-4) → 5-[(1S,3aS,5R,6S,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-1-(dimethyl-phenyl-silanyl)-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid methyl ester (127744-14-3)

Guidance literature:

Multi-step reaction with 6 steps

1: LDA / tetrahydrofuran / 1.) -78 deg C, 20 min, 2.) -78 deg C, 3 min

2: Et₃N / CH₂Cl₂ / 1 h / 0 °C

3: DBU / CH₂Cl₂ / 1 h / 0 - 20 °C

4: 80 percent / NaBH₄, CeCl₃ / methanol / 0.08 h / 0 °C

5: 93 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

6: 58 percent / tetrahydrofuran; diethyl ether; pentane / 2 h / 0 °C

With dmap; sodium tetrahydroborate; cerium(III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; pentane;

DOI:10.1039/a804274h

Reference yield:

5-[(1R,3aS,5R,6S,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-1-hydroxy-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid methyl ester (127744-10-9,127761-37-9) → 5-[(1S,3aS,5R,6S,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-1-(dimethyl-phenyl-silanyl)-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid methyl ester (127744-14-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

2: 58 percent / tetrahydrofuran; diethyl ether; pentane / 2 h / 0 °C

With dmap; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;

DOI:10.1039/a804274h

upstream raw materials:

5-[(1S,3aR,5S,6R,6aR)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-6-cyano-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid methyl ester

3,4,5,6-tetrahydro-2H-pyran-2-one

methyl 4-formylbutanoate

methyl 5-hydroxypentanoate