tert-Butyl-[(4S,5S)-5-(4-methoxy-phenyl)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-ylmethoxy]-diphenyl-silane

Base Information

• Chemical Name: tert-Butyl-[(4S,5S)-5-(4-methoxy-phenyl)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-ylmethoxy]-diphenyl-silane
• CAS No.: 237736-13-9
• Molecular Formula: C₂₆H₃₀O₅SSi
• Molecular Weight: 482.673

Synonyms:tert-Butyl-[(4S,5S)-5-(4-methoxy-phenyl)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-ylmethoxy]-diphenyl-silane

Chemical Property of tert-Butyl-[(4S,5S)-5-(4-methoxy-phenyl)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-ylmethoxy]-diphenyl-silane

Chemical Property:

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Technology Process of tert-Butyl-[(4S,5S)-5-(4-methoxy-phenyl)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-ylmethoxy]-diphenyl-silane

There total 4 articles about tert-Butyl-[(4S,5S)-5-(4-methoxy-phenyl)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-ylmethoxy]-diphenyl-silane 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: 99.0%

(1S,2S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-(4-methoxy-phenyl)-propane-1,2-diol (237736-12-8) → tert-Butyl-[(4S,5S)-5-(4-methoxy-phenyl)-2-oxo-2λ4-[1,3,2]dioxathiolan-4-ylmethoxy]-diphenyl-silane (237736-13-9)

Guidance literature:

With thionyl chloride; triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(99)00712-1

Reference yield:

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate (24393-56-4) → tert-Butyl-[(4S,5S)-5-(4-methoxy-phenyl)-2-oxo-2λ4-[1,3,2]dioxathiolan-4-ylmethoxy]-diphenyl-silane (237736-13-9)

Guidance literature:

Multi-step reaction with 4 steps

1: AD-mix-α / 2-methyl-propan-2-ol; H2O / Ambient temperature

2: 66 percent / NaBH₄ / tetrahydrofuran / 0 °C

3: 99 percent / imidazole / dimethylformamide / 0 °C

4: 99 percent / SOCl₂, Et₃N / CH₂Cl₂ / 0 °C

With 1H-imidazole; sodium tetrahydroborate; AD-mix-α; thionyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/S0040-4039(99)00712-1

Reference yield:

Ethyl threo-3-(p-methoxyphenyl)-2(R),3(S)-dihydroxypropionate (182268-43-5) → tert-Butyl-[(4S,5S)-5-(4-methoxy-phenyl)-2-oxo-2λ4-[1,3,2]dioxathiolan-4-ylmethoxy]-diphenyl-silane (237736-13-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / NaBH₄ / tetrahydrofuran / 0 °C

2: 99 percent / imidazole / dimethylformamide / 0 °C

3: 99 percent / SOCl₂, Et₃N / CH₂Cl₂ / 0 °C

With 1H-imidazole; sodium tetrahydroborate; thionyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(99)00712-1

upstream raw materials:

(1S,2S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-(4-methoxy-phenyl)-propane-1,2-diol

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Ethyl threo-3-(p-methoxyphenyl)-2(R),3(S)-dihydroxypropionate

(1S,2S)-1-(4-Methoxy-phenyl)-propane-1,2,3-triol

Downstream raw materials:

Carbonic acid (1R,2R)-2-azido-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-ethyl ester phenyl ester

(4R,5R)-5-(tert-butyldiphenylsilyloxymethyl)-4-(4-methoxyphenyl)oxazolidin-2-one

(4R,5R)-cytoxazone

(2R,3R)-3-Azido-3-(4-methoxy-phenyl)-propane-1,2-diol

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