methyl 3-(tert-butyldiphenylsilyloxy)-4-methyl-5-phenylsulfinyl-(3S,4S)-pentanoate

Base Information

Chemical Name:methyl 3-(tert-butyldiphenylsilyloxy)-4-methyl-5-phenylsulfinyl-(3S,4S)-pentanoate
CAS No.:556834-67-4
Molecular Formula:C₂₉H₃₆O₄SSi
Molecular Weight:508.754
Hs Code.:

Synonyms:methyl 3-(tert-butyldiphenylsilyloxy)-4-methyl-5-phenylsulfinyl-(3S,4S)-pentanoate

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Chemical Property of methyl 3-(tert-butyldiphenylsilyloxy)-4-methyl-5-phenylsulfinyl-(3S,4S)-pentanoate

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Technology Process of methyl 3-(tert-butyldiphenylsilyloxy)-4-methyl-5-phenylsulfinyl-(3S,4S)-pentanoate

There total 7 articles about methyl 3-(tert-butyldiphenylsilyloxy)-4-methyl-5-phenylsulfinyl-(3S,4S)-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: 70.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 556834-66-3
methyl 3-hydroxy-4-methyl-5-phenylsulfinyl-(3S,4S)-pentanoate

: 556834-67-4
methyl 3-(tert-butyldiphenylsilyloxy)-4-methyl-5-phenylsulfinyl-(3S,4S)-pentanoate

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1021/jo026802p

Reference yield:

: 121783-49-1
(S)-(+)-2-methyl-3-(phenylthio)propan-1-ol

: 556834-67-4
methyl 3-(tert-butyldiphenylsilyloxy)-4-methyl-5-phenylsulfinyl-(3S,4S)-pentanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -78 - -10 °C

2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

2.2: 1.68 g / tetrahydrofuran / 1 h / -78 °C

3.1: 95 percent / NaIO₄ / methanol; H₂O / 0 - 20 °C

4.1: 80 percent / N-bromosuccinimide; water / toluene / 3 h / 20 °C

5.1: 82 percent / tributyltin hydride; N,N'-azobis(isobutyronitrile) / benzene / 3 h / 80 °C

6.1: 70 percent / imidazole / CH₂Cl₂ / 24 h / 20 °C

With 1H-imidazole; sodium periodate; N-Bromosuccinimide; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; toluene; benzene; 1.1: Swern oxidation / 2.2: Wittig olefination;
DOI:10.1021/jo026802p

Reference yield:

: (S)-2-methyl-3-(phenylsulfanyl)propanal

: 556834-67-4
methyl 3-(tert-butyldiphenylsilyloxy)-4-methyl-5-phenylsulfinyl-(3S,4S)-pentanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 1.68 g / tetrahydrofuran / 1 h / -78 °C

2.1: 95 percent / NaIO₄ / methanol; H₂O / 0 - 20 °C

3.1: 80 percent / N-bromosuccinimide; water / toluene / 3 h / 20 °C

4.1: 82 percent / tributyltin hydride; N,N'-azobis(isobutyronitrile) / benzene / 3 h / 80 °C

5.1: 70 percent / imidazole / CH₂Cl₂ / 24 h / 20 °C

With 1H-imidazole; sodium periodate; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; water; toluene; benzene; 1.2: Wittig olefination;
DOI:10.1021/jo026802p