S-tert-butyl [3R,(S)S]-3-hydroxy-4-[2-(p-tolylsulfinyl)phenyl]butanethioate

Base Information

• Chemical Name: S-tert-butyl [3R,(S)S]-3-hydroxy-4-[2-(p-tolylsulfinyl)phenyl]butanethioate
• CAS No.: 919764-51-5
• Molecular Formula: C₂₁H₂₆O₃S₂
• Molecular Weight: 390.568

Synonyms:S-tert-butyl [3R,(S)S]-3-hydroxy-4-[2-(p-tolylsulfinyl)phenyl]butanethioate

Chemical Property of S-tert-butyl [3R,(S)S]-3-hydroxy-4-[2-(p-tolylsulfinyl)phenyl]butanethioate

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Technology Process of S-tert-butyl [3R,(S)S]-3-hydroxy-4-[2-(p-tolylsulfinyl)phenyl]butanethioate

There total 1 articles about S-tert-butyl [3R,(S)S]-3-hydroxy-4-[2-(p-tolylsulfinyl)phenyl]butanethioate 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%

(1-tert-butylsulfanyl-vinyloxy)trimethylsilane (63584-47-4) + (S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde (794525-98-7) → S-tert-butyl [3S,(S)S]-3-hydroxy-4-[2-(p-tolylsulfinyl)phenyl]butanethioate + S-tert-butyl [3R,(S)S]-3-hydroxy-4-[2-(p-tolylsulfinyl)phenyl]butanethioate (919764-51-5)

Guidance literature:

With ytterbium(III) triflate; In acetonitrile; at -40 ℃; for 1.5h;

DOI:10.1016/j.tet.2006.10.010

Reference yield: 90.0%

S-tert-butyl [3R,(S)S]-3-hydroxy-4-[2-(p-tolylsulfinyl)phenyl]butanethioate (919764-51-5) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → S-tert-butyl [3R,(S)S]-4-[2-(p-tolylsulfinyl)phenyl]-3-(triisopropylsilyloxy)butanethioate (919764-56-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1016/j.tet.2006.10.010

Reference yield:

S-tert-butyl [3R,(S)S]-3-hydroxy-4-[2-(p-tolylsulfinyl)phenyl]butanethioate (919764-51-5) → (S)-4-phenylbutane-1,3-diol (1000771-38-9) + (R)-4-phenylbutane-1,3-diol

Guidance literature:

With hydrogen; nickel; In ethanol; at 20 ℃; Title compound not separated from byproducts;

DOI:10.1016/j.tet.2006.10.010

upstream raw materials:

(1-tert-butylsulfanyl-vinyloxy)trimethylsilane

(S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde

Downstream raw materials:

(S)-4-phenylbutane-1,3-diol

S-tert-butyl [3R,(S)S]-4-[2-(p-tolylsulfinyl)phenyl]-3-(triisopropylsilyloxy)butanethioate

(R)-4-phenyl-3-(triisopropylsilyloxy)butan-1-ol

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