tert-butyl (3R)-3-tert-butyldimethylsilyloxy-4-acetoxy-4-p-tolylsulfenyl-butanoate

Base Information

• Chemical Name: tert-butyl (3R)-3-tert-butyldimethylsilyloxy-4-acetoxy-4-p-tolylsulfenyl-butanoate
• CAS No.: 244217-17-2
• Molecular Formula: C₂₃H₃₈O₅SSi
• Molecular Weight: 454.703

Synonyms:tert-butyl (3R)-3-tert-butyldimethylsilyloxy-4-acetoxy-4-p-tolylsulfenyl-butanoate

Chemical Property of tert-butyl (3R)-3-tert-butyldimethylsilyloxy-4-acetoxy-4-p-tolylsulfenyl-butanoate

Chemical Property:

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Technology Process of tert-butyl (3R)-3-tert-butyldimethylsilyloxy-4-acetoxy-4-p-tolylsulfenyl-butanoate

There total 5 articles about tert-butyl (3R)-3-tert-butyldimethylsilyloxy-4-acetoxy-4-p-tolylsulfenyl-butanoate 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: 78.0%

acetic anhydride (108-24-7) + tert-butyl (-)-(3R,SS)-3-tert-butyldimethylsilyloxy-4-p-tolylsulfinyl-butanoate (188709-46-8) → tert-butyl (3R)-3-tert-butyldimethylsilyloxy-4-acetoxy-4-p-tolylsulfenyl-butanoate (244217-17-2)

Guidance literature:

With sodium acetate; at 135 ℃; for 14h;

DOI:10.1021/jo990245y

Reference yield:

tert-butyl acetoacetate (1694-31-1) → tert-butyl (3R)-3-tert-butyldimethylsilyloxy-4-acetoxy-4-p-tolylsulfenyl-butanoate (244217-17-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / -65 °C

1.2: 77 percent / tetrahydrofuran; hexane / -75 °C

2.1: 66.6 percent / DIBAL-H / toluene; tetrahydrofuran / 0.75 h / -75 - -70 °C

3.1: 88.3 percent / imidazole / dimethylformamide / 15 h / 20 °C

4.1: 78 percent / sodium acetate / 14 h / 135 °C

With 1H-imidazole; n-butyllithium; sodium acetate; diisobutylaluminium hydride; diisopropylamine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene; 1.1: Metallation / 1.2: Alkylation / 2.1: Reduction / 3.1: silylation / 4.1: Pummerer rearrangement;

DOI:10.1021/jo990245y

Reference yield:

(1S,2R,5S,RS)-(+)-Menthyl toluene-p-sulfinate (91796-57-5) → tert-butyl (3R)-3-tert-butyldimethylsilyloxy-4-acetoxy-4-p-tolylsulfenyl-butanoate (244217-17-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / -65 °C

1.2: 77 percent / tetrahydrofuran; hexane / -75 °C

2.1: 66.6 percent / DIBAL-H / toluene; tetrahydrofuran / 0.75 h / -75 - -70 °C

3.1: 88.3 percent / imidazole / dimethylformamide / 15 h / 20 °C

4.1: 78 percent / sodium acetate / 14 h / 135 °C

With 1H-imidazole; n-butyllithium; sodium acetate; diisobutylaluminium hydride; diisopropylamine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene; 1.1: Metallation / 1.2: Alkylation / 2.1: Reduction / 3.1: silylation / 4.1: Pummerer rearrangement;

DOI:10.1021/jo990245y

upstream raw materials:

acetic anhydride

tert-butyl (-)-(3R,S_S)-3-tert-butyldimethylsilyloxy-4-p-tolylsulfinyl-butanoate

tert-butyl acetoacetate

(1S,2R,5S,R_S)-(+)-Menthyl toluene-p-sulfinate

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