(S)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2-phenyl-4,5-dihydro-oxazol-4-yl)-thioacetic acid S-tert-butyl ester

Base Information

• Chemical Name: (S)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2-phenyl-4,5-dihydro-oxazol-4-yl)-thioacetic acid S-tert-butyl ester
• CAS No.: 152495-87-9
• Molecular Formula: C₂₁H₃₃NO₃SSi
• Molecular Weight: 407.649

Synonyms:(S)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2-phenyl-4,5-dihydro-oxazol-4-yl)-thioacetic acid S-tert-butyl ester

Chemical Property of (S)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2-phenyl-4,5-dihydro-oxazol-4-yl)-thioacetic acid S-tert-butyl ester

Chemical Property:

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Technology Process of (S)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2-phenyl-4,5-dihydro-oxazol-4-yl)-thioacetic acid S-tert-butyl ester

There total 2 articles about (S)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2-phenyl-4,5-dihydro-oxazol-4-yl)-thioacetic acid S-tert-butyl 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:

2-phenyl-4(S)-<2-((2-methyl-2-propyl)thio)-2-oxoethyl>-2-oxazoline (102614-13-1) → (S)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2-phenyl-4,5-dihydro-oxazol-4-yl)-thioacetic acid S-tert-butyl ester (152495-87-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 1.) NaHMDS, 2.) 2-(phenylsulfonyl)-3-phenyloxaziridine / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C

2: pyridine

With pyridine; sodium hexamethyldisilazane; N-(benzenesulfonyl)-3-phenyloxaziridine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/jo00075a007

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) + (S)-Hydroxy-((R)-2-phenyl-4,5-dihydro-oxazol-4-yl)-thioacetic acid S-tert-butyl ester (152495-86-8) → (S)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2-phenyl-4,5-dihydro-oxazol-4-yl)-thioacetic acid S-tert-butyl ester (152495-87-9)

Guidance literature:

With pyridine;

DOI:10.1021/jo00075a007

Reference yield: 65.0%

(S)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2-phenyl-4,5-dihydro-oxazol-4-yl)-thioacetic acid S-tert-butyl ester (152495-87-9) → (S)-1-(tert-Butyl-dimethyl-silanyloxy)-1-((R)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propan-2-one (152495-90-4)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1021/jo00075a007

upstream raw materials:

t-butyldimethylsiyl triflate

(S)-Hydroxy-((R)-2-phenyl-4,5-dihydro-oxazol-4-yl)-thioacetic acid S-tert-butyl ester

2-phenyl-4(S)-<2-((2-methyl-2-propyl)thio)-2-oxoethyl>-2-oxazoline

Downstream raw materials:

(S)-2-(tert-Butyl-dimethyl-silanyloxy)-2-((R)-2-phenyl-4,5-dihydro-oxazol-4-yl)-ethanol

(S)-1-(tert-Butyl-dimethyl-silanyloxy)-1-((R)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propan-2-one

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