(+)-<3(S),4(S),S(R)>-tert-butyl 3-(2-methoxyethoxymethoxy)-4-(tert-butyldimethylsiloxy)-5-(p-tolylsulfinyl)pentanoate

Base Information

• Chemical Name: (+)-<3(S),4(S),S(R)>-tert-butyl 3-(2-methoxyethoxymethoxy)-4-(tert-butyldimethylsiloxy)-5-(p-tolylsulfinyl)pentanoate
• CAS No.: 163213-87-4
• Molecular Formula: C₂₆H₄₆O₇SSi
• Molecular Weight: 530.799
• Mol file: 163213-87-4.mol

Synonyms:(+)-<3(S),4(S),S(R)>-tert-butyl 3-(2-methoxyethoxymethoxy)-4-(tert-butyldimethylsiloxy)-5-(p-tolylsulfinyl)pentanoate

Chemical Property of (+)-<3(S),4(S),S(R)>-tert-butyl 3-(2-methoxyethoxymethoxy)-4-(tert-butyldimethylsiloxy)-5-(p-tolylsulfinyl)pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-<3(S),4(S),S(R)>-tert-butyl 3-(2-methoxyethoxymethoxy)-4-(tert-butyldimethylsiloxy)-5-(p-tolylsulfinyl)pentanoate

There total 10 articles about (+)-<3(S),4(S),S(R)>-tert-butyl 3-(2-methoxyethoxymethoxy)-4-(tert-butyldimethylsiloxy)-5-(p-tolylsulfinyl)pentanoate 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: 79.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (+)-<3(S),4(S),S(R)>-tert-butyl 3-(2-methoxyethoxymethoxy)-4-hydroxy-5-(p-tolylsulfinyl)pentanoate (163213-83-0) → (+)-<3(S),4(S),S(R)>-tert-butyl 3-(2-methoxyethoxymethoxy)-4-(tert-butyldimethylsiloxy)-5-(p-tolylsulfinyl)pentanoate (163213-87-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 50 ℃; for 36h;

DOI:10.1016/0957-4166(94)80083-9

Reference yield:

(+)(R) tert-butyl 3-oxo-4-(p-tolylsulfinyl)butyrate (142176-64-5) → (+)-<3(S),4(S),S(R)>-tert-butyl 3-(2-methoxyethoxymethoxy)-4-(tert-butyldimethylsiloxy)-5-(p-tolylsulfinyl)pentanoate (163213-87-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 78 percent / DIBAL / tetrahydrofuran; toluene / 0.5 h / -78 °C

2: diisopropylethyl amine / CH₂Cl₂ / 48 h / Ambient temperature

3: AcONa / 8 h / Heating

4: 91 percent / Raney Ni / ethanol / Ambient temperature

5: 92 percent / DIBAL / tetrahydrofuran; toluene / 0.75 h / -78 - 0 °C

6: pyridinium dichromate / dimethylformamide / 15 h / Ambient temperature

7: diethyl ether / 0 °C

8: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 15 min

9: 88 percent / DIBAL / tetrahydrofuran; toluene / 0.17 h / -78 °C

10: 79 percent / imidazole / dimethylformamide / 36 h / 50 °C

With 1H-imidazole; dipyridinium dichromate; sodium acetate; nickel; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0957-4166(94)80083-9

Reference yield:

(+)<3(S),S(R)> tert-butyl 3-hydroxy-4-(p-tolylsulfinyl)butyrate (142176-68-9) → (+)-<3(S),4(S),S(R)>-tert-butyl 3-(2-methoxyethoxymethoxy)-4-(tert-butyldimethylsiloxy)-5-(p-tolylsulfinyl)pentanoate (163213-87-4)

Guidance literature:

Multi-step reaction with 9 steps

1: diisopropylethyl amine / CH₂Cl₂ / 48 h / Ambient temperature

2: AcONa / 8 h / Heating

3: 91 percent / Raney Ni / ethanol / Ambient temperature

4: 92 percent / DIBAL / tetrahydrofuran; toluene / 0.75 h / -78 - 0 °C

5: pyridinium dichromate / dimethylformamide / 15 h / Ambient temperature

6: diethyl ether / 0 °C

7: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 15 min

8: 88 percent / DIBAL / tetrahydrofuran; toluene / 0.17 h / -78 °C

9: 79 percent / imidazole / dimethylformamide / 36 h / 50 °C

With 1H-imidazole; dipyridinium dichromate; sodium acetate; nickel; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0957-4166(94)80083-9

upstream raw materials:

tert-butyldimethylsilyl chloride

(+)-<3(S),4(S),S(R)>-tert-butyl 3-(2-methoxyethoxymethoxy)-4-hydroxy-5-(p-tolylsulfinyl)pentanoate

(+)(R) tert-butyl 3-oxo-4-(p-tolylsulfinyl)butyrate

(+)<3(S),S(R)> tert-butyl 3-hydroxy-4-(p-tolylsulfinyl)butyrate