(R)-(tert-Butyl-diphenyl-silanyloxy)-((1R,2S,4R)-4-triisopropylsilanyloxy-2-vinyl-cyclopentyl)-acetic acid

Base Information

• Chemical Name: (R)-(tert-Butyl-diphenyl-silanyloxy)-((1R,2S,4R)-4-triisopropylsilanyloxy-2-vinyl-cyclopentyl)-acetic acid
• CAS No.: 468732-86-7
• Molecular Formula: C₃₄H₅₂O₄Si₂
• Molecular Weight: 580.955
• Mol file: 468732-86-7.mol

Synonyms:(R)-(tert-Butyl-diphenyl-silanyloxy)-((1R,2S,4R)-4-triisopropylsilanyloxy-2-vinyl-cyclopentyl)-acetic acid

Chemical Property of (R)-(tert-Butyl-diphenyl-silanyloxy)-((1R,2S,4R)-4-triisopropylsilanyloxy-2-vinyl-cyclopentyl)-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(tert-Butyl-diphenyl-silanyloxy)-((1R,2S,4R)-4-triisopropylsilanyloxy-2-vinyl-cyclopentyl)-acetic acid

There total 6 articles about (R)-(tert-Butyl-diphenyl-silanyloxy)-((1R,2S,4R)-4-triisopropylsilanyloxy-2-vinyl-cyclopentyl)-acetic acid 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: 90.0%

(3R,4R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-((Z)-(R)-2-triisopropylsilanyloxy-6-trimethylsilanyl-hex-4-enyl)-oxetan-2-one → (R)-(tert-Butyl-diphenyl-silanyloxy)-((1R,2S,4R)-4-triisopropylsilanyloxy-2-vinyl-cyclopentyl)-acetic acid (468732-86-7)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1021/ol026438g

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (R)-(tert-Butyl-diphenyl-silanyloxy)-((1R,2S,4R)-4-triisopropylsilanyloxy-2-vinyl-cyclopentyl)-acetic acid (468732-86-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaI / acetone / Heating

1.2: 2,6-lutidine / CH₂Cl₂ / 0 °C

2.1: HMPA / tetrahydrofuran / -20 °C

3.1: DIBAL-H / CH₂Cl₂ / -78 °C

4.1: ZnCl₂ / CH₂Cl₂ / 96 h / 23 °C

5.1: 80 percent / Grubbs' imidazolylidene catalyst / CH₂Cl₂ / 18 h / Heating

6.1: 90 percent / TiCl₄ / CH₂Cl₂ / 2 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; titanium tetrachloride; diisobutylaluminium hydride; sodium iodide; zinc(II) chloride; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1021/ol026438g

Reference yield:

(R)-3-Triisopropylsilanyloxy-hex-5-enal (468732-83-4) → (R)-(tert-Butyl-diphenyl-silanyloxy)-((1R,2S,4R)-4-triisopropylsilanyloxy-2-vinyl-cyclopentyl)-acetic acid (468732-86-7)

Guidance literature:

Multi-step reaction with 3 steps

1: ZnCl₂ / CH₂Cl₂ / 96 h / 23 °C

2: 80 percent / Grubbs' imidazolylidene catalyst / CH₂Cl₂ / 18 h / Heating

3: 90 percent / TiCl₄ / CH₂Cl₂ / 2 h / -78 °C

With titanium tetrachloride; zinc(II) chloride; Grubbs catalyst first generation; In dichloromethane;

DOI:10.1021/ol026438g

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

(R)-3-Triisopropylsilanyloxy-hex-5-enal

(R)-3-Triisopropylsilanyloxy-hex-5-enoic acid ethyl ester

(3R,4R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-((R)-2-triisopropylsilanyloxy-pent-4-enyl)-oxetan-2-one