(6E)-(2S,4R,5R)-8-ethoxycarbonyloxy-2-benzyloxy-4,6-dimethyl-5-tert-butyldimethylsiloxy-6-octen-3-one

Base Information

• Chemical Name: (6E)-(2S,4R,5R)-8-ethoxycarbonyloxy-2-benzyloxy-4,6-dimethyl-5-tert-butyldimethylsiloxy-6-octen-3-one
• CAS No.: 880462-50-0
• Molecular Formula: C₂₆H₄₂O₆Si
• Molecular Weight: 478.701

Synonyms:(6E)-(2S,4R,5R)-8-ethoxycarbonyloxy-2-benzyloxy-4,6-dimethyl-5-tert-butyldimethylsiloxy-6-octen-3-one

Chemical Property of (6E)-(2S,4R,5R)-8-ethoxycarbonyloxy-2-benzyloxy-4,6-dimethyl-5-tert-butyldimethylsiloxy-6-octen-3-one

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Technology Process of (6E)-(2S,4R,5R)-8-ethoxycarbonyloxy-2-benzyloxy-4,6-dimethyl-5-tert-butyldimethylsiloxy-6-octen-3-one

There total 3 articles about (6E)-(2S,4R,5R)-8-ethoxycarbonyloxy-2-benzyloxy-4,6-dimethyl-5-tert-butyldimethylsiloxy-6-octen-3-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: 92.0%

(6E)-(2S,4R,5R)-8-ethoxycarbonyloxy-2-benzyloxy-4,6-dimethyl-5-hydroxy-6-octen-3-one (880462-49-7) + t-butyldimethylsiyl triflate (69739-34-0) → (6E)-(2S,4R,5R)-8-ethoxycarbonyloxy-2-benzyloxy-4,6-dimethyl-5-tert-butyldimethylsiloxy-6-octen-3-one (880462-50-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/jo052267s

Reference yield:

(S)-2-benzyloxy-3-pentanone (132489-33-9) → (6E)-(2S,4R,5R)-8-ethoxycarbonyloxy-2-benzyloxy-4,6-dimethyl-5-tert-butyldimethylsiloxy-6-octen-3-one (880462-50-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / c-Hex₂BCl; Et₃N / diethyl ether / cooling

2: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

With 2,6-dimethylpyridine; dicyclohexylboron chloride; triethylamine; In diethyl ether; dichloromethane;

DOI:10.1021/jo052267s

Reference yield:

(2E)-4-ethoxycarbonyloxy-2-methylbut-2-enal (612090-56-9) → (6E)-(2S,4R,5R)-8-ethoxycarbonyloxy-2-benzyloxy-4,6-dimethyl-5-tert-butyldimethylsiloxy-6-octen-3-one (880462-50-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / c-Hex₂BCl; Et₃N / diethyl ether / cooling

2: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

With 2,6-dimethylpyridine; dicyclohexylboron chloride; triethylamine; In diethyl ether; dichloromethane;

DOI:10.1021/jo052267s

upstream raw materials:

(6E)-(2S,4R,5R)-8-ethoxycarbonyloxy-2-benzyloxy-4,6-dimethyl-5-hydroxy-6-octen-3-one

t-butyldimethylsiyl triflate

(S)-2-benzyloxy-3-pentanone

(2E)-4-ethoxycarbonyloxy-2-methylbut-2-enal

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