1-[(1R,2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-oxo-hexahydro-1λ⁴-thiopyran-2-yl]-propan-1-one

Base Information

• Chemical Name: 1-[(1R,2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-oxo-hexahydro-1λ⁴-thiopyran-2-yl]-propan-1-one
• CAS No.: 146698-25-1
• Molecular Formula: C₂₄H₃₂O₃SSi
• Molecular Weight: 428.668

Synonyms:1-[(1R,2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-oxo-hexahydro-1λ⁴-thiopyran-2-yl]-propan-1-one

Chemical Property of 1-[(1R,2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-oxo-hexahydro-1λ⁴-thiopyran-2-yl]-propan-1-one

Chemical Property:

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Technology Process of 1-[(1R,2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-oxo-hexahydro-1λ⁴-thiopyran-2-yl]-propan-1-one

There total 1 articles about 1-[(1R,2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-oxo-hexahydro-1λ⁴-thiopyran-2-yl]-propan-1-one 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: 86.0%

Ethyl propionate (105-37-3,20741-13-3) + 4-(tert-butyldiphenylsiloxy)thiane 1-oxide (141246-72-2) → 1-[(1R,2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-oxo-hexahydro-1λ4-thiopyran-2-yl]-propan-1-one (146698-25-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

Reference yield: 75.0%

1-[(1R,2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-oxo-hexahydro-1λ4-thiopyran-2-yl]-propan-1-one (146698-25-1) → (S)-1-[(1R,2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-oxo-hexahydro-1λ4-thiopyran-2-yl]-propan-1-ol (146698-28-4,146728-38-3)

Guidance literature:

With diisobutylaluminium hydride; zinc(II) chloride; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)60589-0

Reference yield:

1-[(1R,2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-oxo-hexahydro-1λ4-thiopyran-2-yl]-propan-1-one (146698-25-1) → (S)-1-[(2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-tetrahydro-thiopyran-2-yl]-propan-1-ol (146698-31-9,146728-42-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 25 percent / DIBAL / tetrahydrofuran; hexane / 0.25 h / -78 °C

2: 52 percent / BH₃ / tetrahydrofuran / Ambient temperature

With borane; diisobutylaluminium hydride; In tetrahydrofuran; hexane;

upstream raw materials:

Ethyl propionate

4-(tert-butyldiphenylsiloxy)thiane 1-oxide

Downstream raw materials:

(S)-1-[(1R,2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-oxo-hexahydro-1λ⁴-thiopyran-2-yl]-propan-1-ol

(R)-1-[(2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-tetrahydro-thiopyran-2-yl]-propan-1-ol

(S)-1-[(2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-tetrahydro-thiopyran-2-yl]-propan-1-ol

tert-Butyl-[(S)-1-((2S,3S)-3-ethyl-oxiranylmethyl)-3-methylsulfanyl-propoxy]-diphenyl-silane

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