(3E,5S,6R,7S)-8-benzyloxy-6-(tert-butyldimethylsilanyloxy)-5,7-dimethyl-oct-3-enoic acid methyl ester

Base Information

• Chemical Name: (3E,5S,6R,7S)-8-benzyloxy-6-(tert-butyldimethylsilanyloxy)-5,7-dimethyl-oct-3-enoic acid methyl ester
• CAS No.: 444109-26-6
• Molecular Formula: C₂₄H₄₀O₄Si
• Molecular Weight: 420.665

Synonyms:(3E,5S,6R,7S)-8-benzyloxy-6-(tert-butyldimethylsilanyloxy)-5,7-dimethyl-oct-3-enoic acid methyl ester

Chemical Property of (3E,5S,6R,7S)-8-benzyloxy-6-(tert-butyldimethylsilanyloxy)-5,7-dimethyl-oct-3-enoic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (3E,5S,6R,7S)-8-benzyloxy-6-(tert-butyldimethylsilanyloxy)-5,7-dimethyl-oct-3-enoic acid methyl ester

There total 3 articles about (3E,5S,6R,7S)-8-benzyloxy-6-(tert-butyldimethylsilanyloxy)-5,7-dimethyl-oct-3-enoic acid methyl ester 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%

t-butyldimethylsiyl triflate (69739-34-0) + (E)-(5S,6R,7S)-8-Benzyloxy-6-hydroxy-5,7-dimethyl-oct-3-enoic acid methyl ester (184528-50-5) → (3E,5S,6R,7S)-8-benzyloxy-6-(tert-butyldimethylsilanyloxy)-5,7-dimethyl-oct-3-enoic acid methyl ester (444109-26-6)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/ja043168j

Reference yield:

(2S)-3-(benzyloxy)-2-methylpropanal (79027-28-4) → (3E,5S,6R,7S)-8-benzyloxy-6-(tert-butyldimethylsilanyloxy)-5,7-dimethyl-oct-3-enoic acid methyl ester (444109-26-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / TiCl₄ / CH₂Cl₂ / -78 - -20 °C

2: 97 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 20 °C

With 2,6-dimethylpyridine; titanium tetrachloride; In dichloromethane;

DOI:10.1021/ja043168j

Reference yield:

methyl (3S,4E)-3-(dimethylphenylsilyl)-4-hexenoate (136314-66-4) → (3E,5S,6R,7S)-8-benzyloxy-6-(tert-butyldimethylsilanyloxy)-5,7-dimethyl-oct-3-enoic acid methyl ester (444109-26-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / TiCl₄ / CH₂Cl₂ / -78 - -20 °C

2: 97 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 20 °C

With 2,6-dimethylpyridine; titanium tetrachloride; In dichloromethane;

DOI:10.1021/ja043168j

upstream raw materials:

t-butyldimethylsiyl triflate

(E)-(5S,6R,7S)-8-Benzyloxy-6-hydroxy-5,7-dimethyl-oct-3-enoic acid methyl ester

(2S)-3-(benzyloxy)-2-methylpropanal

methyl (3S,4E)-3-(dimethylphenylsilyl)-4-hexenoate

Downstream raw materials:

(2S,3R,4S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-pentanal

(R)-2-[(2S,4S,5S,6S)-6-((3Z,8Z)-(2S,5S,6S,7S)-6-Hydroxy-9-iodo-2-methoxymethoxy-5,7-dimethyl-deca-3,8-dienyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionic acid methyl ester

(2R,3S,4S,5S,7S,8Z,10S,11S,12S,13Z)-14-iodo-3,5-[(S)-4-methoxybenzilidenedioxy]-7,11-bis-methoxymethoxy-2,4,10,12-tetramethylpentadeca-8,13-dienoic acid methyl ester

(R)-2-[(2S,4S,5S,6S)-6-[(Z)-(2S,5S,6R,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5,7-dimethyl-9-trimethylsilanyl-dec-8-en-3-ynyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionaldehyde

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