(R_s)-1-(tert-butyldimethylsilyl)oxy-9-(tetrahydropyran-2-yl)oxy-4-<(p-tolyl)sulfinyl>nonan-5-one

Base Information

• Chemical Name: (R_s)-1-(tert-butyldimethylsilyl)oxy-9-(tetrahydropyran-2-yl)oxy-4-<(p-tolyl)sulfinyl>nonan-5-one
• CAS No.: 99277-40-4
• Molecular Formula: C₂₇H₄₆O₅SSi
• Molecular Weight: 510.811

Synonyms:(R_s)-1-(tert-butyldimethylsilyl)oxy-9-(tetrahydropyran-2-yl)oxy-4-<(p-tolyl)sulfinyl>nonan-5-one

Chemical Property of (R_s)-1-(tert-butyldimethylsilyl)oxy-9-(tetrahydropyran-2-yl)oxy-4-<(p-tolyl)sulfinyl>nonan-5-one

Chemical Property:

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Technology Process of (R_s)-1-(tert-butyldimethylsilyl)oxy-9-(tetrahydropyran-2-yl)oxy-4-<(p-tolyl)sulfinyl>nonan-5-one

There total 7 articles about (R_s)-1-(tert-butyldimethylsilyl)oxy-9-(tetrahydropyran-2-yl)oxy-4-<(p-tolyl)sulfinyl>nonan-5-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: 56.0%

methyl 4-<(tetrahydropyran-2-yl)oxy>valerate (99277-39-1) + (Rs)-1-(tert-butyldimethylsilyl)oxy-4-<(p-tolyl)sulfinyl>butane (99277-38-0) → (Rs)-1-(tert-butyldimethylsilyl)oxy-9-(tetrahydropyran-2-yl)oxy-4-<(p-tolyl)sulfinyl>nonan-5-one (99277-40-4)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diethylamide; In tetrahydrofuran; at -70 ℃;

DOI:10.1016/S0040-4039(00)98967-6

Reference yield:

(Rs)-4-<(p-tolyl)sulfinyl>butan-1-ol (99277-37-9) → (Rs)-1-(tert-butyldimethylsilyl)oxy-9-(tetrahydropyran-2-yl)oxy-4-<(p-tolyl)sulfinyl>nonan-5-one (99277-40-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / imidazole / dimethylformamide / 4 h / Ambient temperature

2: 1.) LiNEt₂; 2.) HMPA / 1.) THF, -40 deg C, 30 min; 2.) -70 - 0 deg C,

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diethylamide; In N,N-dimethyl-formamide;

Reference yield:

(Rs)-1-(tetrahydropyran-2-yl)oxy-4-<(p-tolyl)sulfinyl>butane (99277-36-8) → (Rs)-1-(tert-butyldimethylsilyl)oxy-9-(tetrahydropyran-2-yl)oxy-4-<(p-tolyl)sulfinyl>nonan-5-one (99277-40-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / TSA / methanol / 4.5 h / Ambient temperature

2: 92 percent / imidazole / dimethylformamide / 4 h / Ambient temperature

3: 1.) LiNEt₂; 2.) HMPA / 1.) THF, -40 deg C, 30 min; 2.) -70 - 0 deg C,

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diethylamide; In methanol; N,N-dimethyl-formamide;

upstream raw materials:

methyl 4-<(tetrahydropyran-2-yl)oxy>valerate

(R_s)-1-(tert-butyldimethylsilyl)oxy-4-<(p-tolyl)sulfinyl>butane

3,4-dihydro-2H-pyran

methyl 5-hydroxypentanoate

Downstream raw materials:

(R_s)-1-hydroxy-9-(tetrahydropyran-2-yl)oxy-4-<(p-tolyl)sulfinyl>nonan-5-one

(R_s)-3,4-dihydro-6-(4-hydroxybutyl)-5-(p-tolyl)sulfinyl-2H-pyran

(R_s)-3,4-dihydro-6-<4-(tetrahydropyran-2-yl)oxobutyl>-5-(p-tolyl)sulfinyl-2H-pyran

(+)-(S)-1,7-Dioxaspiro<5.5>undecane

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