{(1S,2S,5R)-2-[6-(tert-Butyl-diphenyl-silanyloxy)-hexyl]-5-triethylsilanyloxy-cyclopentyl}-acetic acid methyl ester

Base Information

• Chemical Name: {(1S,2S,5R)-2-[6-(tert-Butyl-diphenyl-silanyloxy)-hexyl]-5-triethylsilanyloxy-cyclopentyl}-acetic acid methyl ester
• CAS No.: 827325-82-6
• Molecular Formula: C₃₆H₅₈O₄Si₂
• Molecular Weight: 611.025
• Mol file: 827325-82-6.mol

Synonyms:{(1S,2S,5R)-2-[6-(tert-Butyl-diphenyl-silanyloxy)-hexyl]-5-triethylsilanyloxy-cyclopentyl}-acetic acid methyl ester

Chemical Property of {(1S,2S,5R)-2-[6-(tert-Butyl-diphenyl-silanyloxy)-hexyl]-5-triethylsilanyloxy-cyclopentyl}-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(1S,2S,5R)-2-[6-(tert-Butyl-diphenyl-silanyloxy)-hexyl]-5-triethylsilanyloxy-cyclopentyl}-acetic acid methyl ester

There total 11 articles about {(1S,2S,5R)-2-[6-(tert-Butyl-diphenyl-silanyloxy)-hexyl]-5-triethylsilanyloxy-cyclopentyl}-acetic 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:

triethylsilyl chloride (994-30-9) + {(1S,2S,5R)-2-[6-(tert-Butyl-diphenyl-silanyloxy)-hexyl]-5-hydroxy-cyclopentyl}-acetic acid methyl ester (894351-73-6) → {(1S,2S,5R)-2-[6-(tert-Butyl-diphenyl-silanyloxy)-hexyl]-5-triethylsilanyloxy-cyclopentyl}-acetic acid methyl ester (827325-82-6)

Guidance literature:

DOI:10.1055/s-2004-834794

Reference yield:

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate (60410-16-4) → {(1S,2S,5R)-2-[6-(tert-Butyl-diphenyl-silanyloxy)-hexyl]-5-triethylsilanyloxy-cyclopentyl}-acetic acid methyl ester (827325-82-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: t-BuMgCl / tetrahydrofuran / 0.17 h / 0 °C

1.2: CuCN / tetrahydrofuran / 4 h / -18 °C

1.3: 77 percent / Ph₃P; DIAD / toluene / 5 h / -78 °C

2.1: 95 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 20 °C

3.1: 97 percent / Hg(OAc)2 / benzene / 70 h / 180 - 190 °C

4.1: 90 percent / Jones reagent / acetone / 0.17 h / cooling

5.1: 86 percent / NaHCO₃; KI; I₂ / diethyl ether; tetrahydrofuran; H₂O / 16 h / 20 °C

6.1: 97 percent / Bu₃SnH; AIBN / benzene / 1 h / Heating

7.1: LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 3 h / 20 °C

8.1: diethyl ether / 0.08 h / -18 °C

9.1: 55 mg / imidazole / dimethylformamide / 14 h / 20 °C

With 1H-imidazole; lithium hydroxide; jones reagent; 2,2'-azobis(isobutyronitrile); tert-butylmagnesium chloride; mercury(II) diacetate; iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; potassium iodide; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide; acetone; benzene; 1.3: Mitsunobu reaction / 3.1: Claisen rearrangement / 4.1: Jones oxidation;

DOI:10.1016/j.tet.2006.03.001

Reference yield:

C22H31ClMgOSi → {(1S,2S,5R)-2-[6-(tert-Butyl-diphenyl-silanyloxy)-hexyl]-5-triethylsilanyloxy-cyclopentyl}-acetic acid methyl ester (827325-82-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: t-BuMgCl / tetrahydrofuran / 0.17 h / 0 °C

1.2: CuCN / tetrahydrofuran / 4 h / -18 °C

1.3: 77 percent / Ph₃P; DIAD / toluene / 5 h / -78 °C

2.1: 95 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 20 °C

3.1: 97 percent / Hg(OAc)2 / benzene / 70 h / 180 - 190 °C

4.1: 90 percent / Jones reagent / acetone / 0.17 h / cooling

5.1: 86 percent / NaHCO₃; KI; I₂ / diethyl ether; tetrahydrofuran; H₂O / 16 h / 20 °C

6.1: 97 percent / Bu₃SnH; AIBN / benzene / 1 h / Heating

7.1: LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 3 h / 20 °C

8.1: diethyl ether / 0.08 h / -18 °C

9.1: 55 mg / imidazole / dimethylformamide / 14 h / 20 °C

With 1H-imidazole; lithium hydroxide; jones reagent; 2,2'-azobis(isobutyronitrile); tert-butylmagnesium chloride; mercury(II) diacetate; iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; potassium iodide; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide; acetone; benzene; 1.3: Mitsunobu reaction / 3.1: Claisen rearrangement / 4.1: Jones oxidation;

DOI:10.1016/j.tet.2006.03.001

upstream raw materials:

triethylsilyl chloride

{(1S,2S,5R)-2-[6-(tert-Butyl-diphenyl-silanyloxy)-hexyl]-5-hydroxy-cyclopentyl}-acetic acid methyl ester

(3aS,4S,6S,6aS)-4-[6-(tert-Butyl-diphenyl-silanyloxy)-hexyl]-6-iodo-hexahydro-cyclopenta[b]furan-2-one

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

Downstream raw materials:

{(1S,2S,5R)-2-[6-(tert-Butyl-diphenyl-silanyloxy)-hexyl]-5-triethylsilanyloxy-cyclopentyl}-acetaldehyde

C₃₈H₆₂O₂Si₂