(2S,4R,5R,6E,8E)-10-(tert-butyldimethylsilyloxy)-5-hydroxy-4,7-dimethyl-3-oxodeca-6,8-dien-2-yl benzoate

Base Information

• Chemical Name: (2S,4R,5R,6E,8E)-10-(tert-butyldimethylsilyloxy)-5-hydroxy-4,7-dimethyl-3-oxodeca-6,8-dien-2-yl benzoate
• CAS No.: 1185341-38-1
• Molecular Formula: C₂₅H₃₈O₅Si
• Molecular Weight: 446.659

Synonyms:(2S,4R,5R,6E,8E)-10-(tert-butyldimethylsilyloxy)-5-hydroxy-4,7-dimethyl-3-oxodeca-6,8-dien-2-yl benzoate

Chemical Property of (2S,4R,5R,6E,8E)-10-(tert-butyldimethylsilyloxy)-5-hydroxy-4,7-dimethyl-3-oxodeca-6,8-dien-2-yl benzoate

Chemical Property:

Purity/Quality:

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Technology Process of (2S,4R,5R,6E,8E)-10-(tert-butyldimethylsilyloxy)-5-hydroxy-4,7-dimethyl-3-oxodeca-6,8-dien-2-yl benzoate

There total 1 articles about (2S,4R,5R,6E,8E)-10-(tert-butyldimethylsilyloxy)-5-hydroxy-4,7-dimethyl-3-oxodeca-6,8-dien-2-yl benzoate 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: 97.0%

(S)-2-benzoyloxypentan-3-one (160666-92-2) + (2E,4E)-6-(tert-butyldimethylsilyloxy)-3-methylhexa-2,4-dienal (165604-95-5) → (2S,4R,5R,6E,8E)-10-(tert-butyldimethylsilyloxy)-5-hydroxy-4,7-dimethyl-3-oxodeca-6,8-dien-2-yl benzoate (1185341-38-1)

Guidance literature:

(S)-2-benzoyloxypentan-3-one; With N,N-dimethyl-ethanamine; dicyclohexylboron chloride; In diethyl ether; at -78 - 0 ℃;

(2E,4E)-6-(tert-butyldimethylsilyloxy)-3-methylhexa-2,4-dienal; In diethyl ether; at -78 - -22 ℃; for 17h;

With dihydrogen peroxide; In methanol; water; at 0 ℃; optical yield given as %de; diastereoselective reaction; aq. phosphate buffer;

DOI:10.1021/ja9056163

Reference yield: 87.0%

(2S,4R,5R,6E,8E)-10-(tert-butyldimethylsilyloxy)-5-hydroxy-4,7-dimethyl-3-oxodeca-6,8-dien-2-yl benzoate (1185341-38-1) + t-butyldimethylsiyl triflate (69739-34-0) → (2S,4R,5R,6E,8E)-5,10-bis(tert-butyldimethylsilyloxy)-4,7-dimethyl-3-oxodeca-6,8-dien-2-yl benzoate (1180131-42-3)

Guidance literature:

With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; In dichloromethane; at -78 ℃;

DOI:10.1021/ja9056163 DOI:10.1021/jo100201f

Reference yield:

(2S,4R,5R,6E,8E)-10-(tert-butyldimethylsilyloxy)-5-hydroxy-4,7-dimethyl-3-oxodeca-6,8-dien-2-yl benzoate (1185341-38-1) + (3,4-dimethoxoxyphenyl)methyl 2,2,2-trichloroacetimidate (905589-59-5) → C34H48O7Si (1221294-62-7)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 23h;

DOI:10.1021/jo100201f

upstream raw materials:

(S)-2-benzoyloxypentan-3-one

(2E,4E)-6-(tert-butyldimethylsilyloxy)-3-methylhexa-2,4-dienal

Downstream raw materials:

(2S,4R,5R,6E,8E)-5,10-bis(tert-butyldimethylsilyloxy)-4,7-dimethyl-3-oxodeca-6,8-dien-2-yl benzoate

C₃₄H₄₈O₇Si

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