(E)-(4R,7R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-oct-2-enoic acid 2-benzenesulfonyl-ethyl ester

Base Information

• Chemical Name: (E)-(4R,7R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-oct-2-enoic acid 2-benzenesulfonyl-ethyl ester
• CAS No.: 134852-87-2
• Molecular Formula: C₂₂H₃₆O₆SSi
• Molecular Weight: 456.676
• Mol file: 134852-87-2.mol

Synonyms:(E)-(4R,7R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-oct-2-enoic acid 2-benzenesulfonyl-ethyl ester

Chemical Property of (E)-(4R,7R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-oct-2-enoic acid 2-benzenesulfonyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4R,7R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-oct-2-enoic acid 2-benzenesulfonyl-ethyl ester

There total 9 articles about (E)-(4R,7R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-oct-2-enoic acid 2-benzenesulfonyl-ethyl 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: 99.0%

(E)-(4R,7R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-(2-ethoxy-ethoxy)-oct-2-enoic acid 2-benzenesulfonyl-ethyl ester → (E)-(4R,7R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-oct-2-enoic acid 2-benzenesulfonyl-ethyl ester (134852-87-2)

Guidance literature:

With magnesium bromide; In diethyl ether;

DOI:10.1016/0040-4039(91)80367-F

Reference yield:

methyl 7(R)-acetoxy-4(R)-tert. butyldimethylsilyloxy-2(E)-octenoate (134828-70-9) → (E)-(4R,7R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-oct-2-enoic acid 2-benzenesulfonyl-ethyl ester (134852-87-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / NaOMe, MeOH / 0 °C

2: 99 percent / PPTS / CH₂Cl₂

3: 98 percent / LiOH / tetrahydrofuran; H₂O

4: 68 percent / dicyclohexylcarbodiimide, DMAP / CH₂Cl₂

5: 99 percent / MgBr₂ / diethyl ether

With methanol; dmap; lithium hydroxide; sodium methylate; pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide; magnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1016/0040-4039(91)80367-F

Reference yield:

Acetic acid (R)-3-[(2R,3S)-3-(2-diazo-acetyl)-oxiranyl]-1-methyl-propyl ester → (E)-(4R,7R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-oct-2-enoic acid 2-benzenesulfonyl-ethyl ester (134852-87-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 2.) imidazole / 1.) hν, 2.) DMF

2: 85 percent / NaOMe, MeOH / 0 °C

3: 99 percent / PPTS / CH₂Cl₂

4: 98 percent / LiOH / tetrahydrofuran; H₂O

5: 68 percent / dicyclohexylcarbodiimide, DMAP / CH₂Cl₂

6: 99 percent / MgBr₂ / diethyl ether

With 1H-imidazole; methanol; dmap; lithium hydroxide; sodium methylate; pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide; magnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1016/0040-4039(91)80367-F

upstream raw materials:

2-(phenylsulfonyl)ethanol

Acetic acid (E)-(R)-6-hydroxy-1-methyl-hex-4-enyl ester

Acetic acid (R)-3-((2R,3R)-3-hydroxymethyl-oxiranyl)-1-methyl-propyl ester

(E)-(4R,7R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-oct-2-enoic acid methyl ester

Downstream raw materials:

(-)-(RRR)-Colletallol

(E)-(4R,7R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-((E)-(R)-5-hydroxy-hex-2-enoyloxy)-oct-2-enoic acid 2-benzenesulfonyl-ethyl ester

(E)-(4R,7R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-oct-2-enoic acid (E)-(1R,4R)-6-(2-benzenesulfonyl-ethoxycarbonyl)-4-(tert-butyl-dimethyl-silanyloxy)-1-methyl-hex-5-enyl ester

5R,8R,13R,16R pyrenophorol