(2S,4R,5R,6S)-2-tert-butyldimethylsilyloxy-6-tert-butyldiphenylsilyloxy-4-hexyl-5-hydroxy-3-heptanone

Base Information

• Chemical Name: (2S,4R,5R,6S)-2-tert-butyldimethylsilyloxy-6-tert-butyldiphenylsilyloxy-4-hexyl-5-hydroxy-3-heptanone
• CAS No.: 245073-33-0
• Molecular Formula: C₃₅H₅₈O₄Si₂
• Molecular Weight: 599.014

Synonyms:(2S,4R,5R,6S)-2-tert-butyldimethylsilyloxy-6-tert-butyldiphenylsilyloxy-4-hexyl-5-hydroxy-3-heptanone

Chemical Property of (2S,4R,5R,6S)-2-tert-butyldimethylsilyloxy-6-tert-butyldiphenylsilyloxy-4-hexyl-5-hydroxy-3-heptanone

Chemical Property:

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Technology Process of (2S,4R,5R,6S)-2-tert-butyldimethylsilyloxy-6-tert-butyldiphenylsilyloxy-4-hexyl-5-hydroxy-3-heptanone

There total 4 articles about (2S,4R,5R,6S)-2-tert-butyldimethylsilyloxy-6-tert-butyldiphenylsilyloxy-4-hexyl-5-hydroxy-3-heptanone 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: 84.0%

(S)-2-(O-tert-butyldiphenylsilyloxy)propanal (87696-33-1) + (S)-2-tert-Butyldimethylsilyloxy-3-decanone (312538-66-2) → (2S,4R,5R,6S)-2-tert-butyldimethylsilyloxy-6-tert-butyldiphenylsilyloxy-4-hexyl-5-hydroxy-3-heptanone (245073-33-0)

Guidance literature:

(S)-2-tert-Butyldimethylsilyloxy-3-decanone; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃;

(S)-2-(O-tert-butyldiphenylsilyloxy)propanal; In dichloromethane;

DOI:10.1016/S0040-4039(99)00987-9

Reference yield:

n-hexyllithium (21369-64-2) → (2S,4R,5R,6S)-2-tert-butyldimethylsilyloxy-6-tert-butyldiphenylsilyloxy-4-hexyl-5-hydroxy-3-heptanone (245073-33-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 77 percent / tetrahydrofuran / -78 °C

2.1: TiCl₄; DIPEA / CH₂Cl₂ / -78 °C

2.2: 84 percent / CH₂Cl₂

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1.1: Alkylation / 2.1: Metallation / 2.2: Addition;

DOI:10.1016/S0040-4039(99)00987-9

Reference yield:

(S)-2-(tert-butyldimethylsilyloxy)-N,N-tetramethylenepropanamide (188659-92-9) → (2S,4R,5R,6S)-2-tert-butyldimethylsilyloxy-6-tert-butyldiphenylsilyloxy-4-hexyl-5-hydroxy-3-heptanone (245073-33-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 77 percent / tetrahydrofuran / -78 °C

2.1: TiCl₄; DIPEA / CH₂Cl₂ / -78 °C

2.2: 84 percent / CH₂Cl₂

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1.1: Alkylation / 2.1: Metallation / 2.2: Addition;

DOI:10.1016/S0040-4039(99)00987-9

upstream raw materials:

(S)-2-(O-tert-butyldiphenylsilyloxy)propanal

(S)-2-tert-Butyldimethylsilyloxy-3-decanone

n-hexyllithium

(S)-2-(tert-butyldimethylsilyloxy)-N,N-tetramethylenepropanamide

Downstream raw materials:

(2S,3R,4R,6S)-6-tert-butyldimethylsilyloxy-2-tert-butyldiphenylsilyloxy-4-hexyl-5-oxo-3-heptanyl 3-methylbutanoate

(2S,4R,5R,6S)-6-tert-butyldiphenylsilyloxy-4-hexyl-2,5-dihydroxy-3-heptanone

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