Acetic acid (E)-(R)-1-[(1R,2R,3aR,5S,6aS)-5-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-octahydro-pentalen-1-yl]-oct-2-enyl ester

Base Information

• Chemical Name: Acetic acid (E)-(R)-1-[(1R,2R,3aR,5S,6aS)-5-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-octahydro-pentalen-1-yl]-oct-2-enyl ester
• CAS No.: 208389-13-3
• Molecular Formula: C₃₄H₄₈O₄Si
• Molecular Weight: 548.838
• Mol file: 208389-13-3.mol

Synonyms:

Chemical Property of Acetic acid (E)-(R)-1-[(1R,2R,3aR,5S,6aS)-5-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-octahydro-pentalen-1-yl]-oct-2-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (E)-(R)-1-[(1R,2R,3aR,5S,6aS)-5-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-octahydro-pentalen-1-yl]-oct-2-enyl ester

There total 3 articles about Acetic acid (E)-(R)-1-[(1R,2R,3aR,5S,6aS)-5-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-octahydro-pentalen-1-yl]-oct-2-enyl 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:

(E)-2-Octenal (2548-87-0) → Acetic acid (E)-(R)-1-[(1R,2R,3aR,5S,6aS)-5-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-octahydro-pentalen-1-yl]-oct-2-enyl ester (208389-13-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Et₂O*BF₃; 2.) aq AcOH / 1.) CH₂Cl₂, -78 deg C, 1 h; 2.) THF, r.t., 12 h

2: 1.) pyridine; 2.) Zn(BH₄)2 / 1.) THF, 16 h, r.t.; 2.) ether, -30 deg C, 6 h

With pyridine; zinc(II) tetrahydroborate; boron trifluoride diethyl etherate; acetic acid;

DOI:10.1002/(SICI)1099-0690(199805)1998:5<805::AID-EJOC805>3.0.CO;2-R

Reference yield:

2-(tert-Butyl-diphenyl-silanyloxy)-5-triethylsilanyloxy-1,2,3,3a,4,6a-hexahydro-pentalene → Acetic acid (E)-(R)-1-[(1R,2R,3aR,5S,6aS)-5-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-octahydro-pentalen-1-yl]-oct-2-enyl ester (208389-13-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Et₂O*BF₃; 2.) aq AcOH / 1.) CH₂Cl₂, -78 deg C, 1 h; 2.) THF, r.t., 12 h

2: 1.) pyridine; 2.) Zn(BH₄)2 / 1.) THF, 16 h, r.t.; 2.) ether, -30 deg C, 6 h

With pyridine; zinc(II) tetrahydroborate; boron trifluoride diethyl etherate; acetic acid;

DOI:10.1002/(SICI)1099-0690(199805)1998:5<805::AID-EJOC805>3.0.CO;2-R

Reference yield:

acetyl chloride (75-36-5) + (1S,3aS,5S,6aS)-5-(tert-Butyl-diphenyl-silanyloxy)-1-((E)-(R)-1-hydroxy-oct-2-enyl)-hexahydro-pentalen-2-one (208389-08-6) → Acetic acid (E)-(R)-1-[(1R,2R,3aR,5S,6aS)-5-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-octahydro-pentalen-1-yl]-oct-2-enyl ester (208389-13-3) + Acetic acid (E)-(R)-1-[(1R,2S,3aR,5S,6aS)-5-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-octahydro-pentalen-1-yl]-oct-2-enyl ester

Guidance literature:

With pyridine; zinc(II) tetrahydroborate; Yield given. Multistep reaction; 1.) THF, 16 h, r.t.; 2.) ether, -30 deg C, 6 h;

DOI:10.1002/(SICI)1099-0690(199805)1998:5<805::AID-EJOC805>3.0.CO;2-R

upstream raw materials:

acetyl chloride

(1S,3aS,5S,6aS)-5-(tert-Butyl-diphenyl-silanyloxy)-1-((E)-(R)-1-hydroxy-oct-2-enyl)-hexahydro-pentalen-2-one

(E)-2-Octenal

Downstream raw materials:

Benzoic acid (1R,2R,3aR,5S,6aS)-1-((E)-(R)-1-acetoxy-oct-2-enyl)-5-(tert-butyl-diphenyl-silanyloxy)-octahydro-pentalen-2-yl ester

[(3aS,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-hexahydro-pentalen-(2E)-ylidene]-acetic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

[(3aS,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-hexahydro-pentalen-(2Z)-ylidene]-acetic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

[(3aS,4R,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-pentalen-(2E)-ylidene]-acetic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester