(Z)-7-[(1R,2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester

Base Information

• Chemical Name: (Z)-7-[(1R,2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester
• CAS No.: 92596-30-0
• Molecular Formula: C₃₆H₅₀O₅Si
• Molecular Weight: 590.875
• Mol file: 92596-30-0.mol

Synonyms:

Chemical Property of (Z)-7-[(1R,2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-7-[(1R,2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester

There total 1 articles about (Z)-7-[(1R,2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic 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:

(3aR,4S,5R,6aS)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one (92596-29-7) → (Z)-7-[(1R,2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester (92596-30-0)

Guidance literature:

DOI:10.1246/cl.1984.1069

Reference yield:

(Z)-7-[(1R,2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester (92596-30-0) → isocarbacyclin (88931-51-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) thexylborane, 2.) 5M NaOH, 30percent H₂O₂, 3.) Collins reagent, / 1.) -78 to 0 deg C, 1 h, 2.) -10 to 50 deg C,

2: TiCl₄/Zn,

3: 2.) DBU, / 1.) mesylation,

4: 1.) (CF₃CO)2O, NaI, 2.) Zn, / 2.) 60 deg C,

5: n-Bu₄N⁽¹⁺⁾*F^(1-),

6: Collins reagent,

8: Zn(BH₄)2,

9: deprotection,

With sodium hydroxide; zinc(II) tetrahydroborate; Collins oxidation agent; thexylborane; tetrabutyl ammonium fluoride; dihydrogen peroxide; titanium tetrachloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic anhydride; sodium iodide; zinc;

DOI:10.1246/cl.1984.1069

Reference yield:

(Z)-7-[(1R,2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester (92596-30-0) → 5-[(3aS,5R,6S,6aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(tetrahydro-pyran-2-yloxy)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-pentanoic acid methyl ester (92596-35-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) thexylborane, 2.) 5M NaOH, 30percent H₂O₂, 3.) Collins reagent, / 1.) -78 to 0 deg C, 1 h, 2.) -10 to 50 deg C,

2: TiCl₄/Zn,

3: 2.) DBU, / 1.) mesylation,

4: 1.) (CF₃CO)2O, NaI, 2.) Zn, / 2.) 60 deg C,

With sodium hydroxide; Collins oxidation agent; thexylborane; dihydrogen peroxide; titanium tetrachloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic anhydride; sodium iodide; zinc;

DOI:10.1246/cl.1984.1069

upstream raw materials:

(3aR,4S,5R,6aS)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one

Downstream raw materials:

7-[(1R,2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-formyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-6-oxo-heptanoic acid methyl ester

7-[(1S,2S,3R,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-6-hydroxy-heptanoic acid methyl ester

7-[(1S,2S,3R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-6-hydroxy-heptanoic acid methyl ester

isocarbacyclin