(2S,2aS,4R,4aR,5R,6R,7R,7aS,7bR)-5-tert-butyldimethylsiloxy-4-[(S)-hydroxy-[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-6,7-(O-isopropylidenedioxy)decahydroindeno[7,1-bc]furan-2-ol

Base Information

• Chemical Name: (2S,2aS,4R,4aR,5R,6R,7R,7aS,7bR)-5-tert-butyldimethylsiloxy-4-[(S)-hydroxy-[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-6,7-(O-isopropylidenedioxy)decahydroindeno[7,1-bc]furan-2-ol
• CAS No.: 623550-19-6
• Molecular Formula: C₂₉H₄₆O₉Si
• Molecular Weight: 566.764

Synonyms:(2S,2aS,4R,4aR,5R,6R,7R,7aS,7bR)-5-tert-butyldimethylsiloxy-4-[(S)-hydroxy-[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-6,7-(O-isopropylidenedioxy)decahydroindeno[7,1-bc]furan-2-ol

Chemical Property of (2S,2aS,4R,4aR,5R,6R,7R,7aS,7bR)-5-tert-butyldimethylsiloxy-4-[(S)-hydroxy-[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-6,7-(O-isopropylidenedioxy)decahydroindeno[7,1-bc]furan-2-ol

Chemical Property:

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Safty Information:

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Useful:

Technology Process of (2S,2aS,4R,4aR,5R,6R,7R,7aS,7bR)-5-tert-butyldimethylsiloxy-4-[(S)-hydroxy-[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-6,7-(O-isopropylidenedioxy)decahydroindeno[7,1-bc]furan-2-ol

There total 7 articles about (2S,2aS,4R,4aR,5R,6R,7R,7aS,7bR)-5-tert-butyldimethylsiloxy-4-[(S)-hydroxy-[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-6,7-(O-isopropylidenedioxy)decahydroindeno[7,1-bc]furan-2-ol 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: 80.0%

4-bromo-1-methoxy-2-(methoxymethoxy)benzene (623550-16-3) + (2S,2aS,4R,4aS,5R,6R,7R,7aS,7bR)-5-tert-butyldimethylsiloxy-2-hydroxy-6,7-(O-isopropylidenedioxy)decahydroindeno[7,1-bc]furan-4-carbaldehyde (623550-08-3) → (2S,2aS,4R,4aR,5R,6R,7R,7aS,7bR)-5-tert-butyldimethylsiloxy-4-[(S)-hydroxy-[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-6,7-(O-isopropylidenedioxy)decahydroindeno[7,1-bc]furan-2-ol (623550-19-6) + (2S,2aS,4R,4aR,5R,6R,7R,7aS,7bR)-5-tert-butyldimethylsiloxy-4-[(R)-hydroxy-[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-6,7-(O-isopropylidenedioxy)decahydroindeno[7,1-bc]furan-2-ol (623550-65-2)

Guidance literature:

4-bromo-1-methoxy-2-(methoxymethoxy)benzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

(2S,2aS,4R,4aS,5R,6R,7R,7aS,7bR)-5-tert-butyldimethylsiloxy-2-hydroxy-6,7-(O-isopropylidenedioxy)decahydroindeno[7,1-bc]furan-4-carbaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

DOI:10.1021/ol035443x

Reference yield:

5-bromo-2-methoxyphenol (37942-01-1) → (2S,2aS,4R,4aR,5R,6R,7R,7aS,7bR)-5-tert-butyldimethylsiloxy-4-[(S)-hydroxy-[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-6,7-(O-isopropylidenedioxy)decahydroindeno[7,1-bc]furan-2-ol (623550-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 88 percent / iPr₂NEt / CH₂Cl₂ / 4 h / 0 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 80 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With n-butyllithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/ol035443x

Reference yield:

2-methoxyphenyl benzoate (531-37-3) → (2S,2aS,4R,4aR,5R,6R,7R,7aS,7bR)-5-tert-butyldimethylsiloxy-4-[(S)-hydroxy-[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-6,7-(O-isopropylidenedioxy)decahydroindeno[7,1-bc]furan-2-ol (623550-19-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Br₂; AcOH / 20 °C

2.1: K₂CO₃ / methanol / 20 °C

3.1: 88 percent / iPr₂NEt / CH₂Cl₂ / 4 h / 0 - 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

4.2: 80 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With n-butyllithium; bromine; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1021/ol035443x

upstream raw materials:

4-bromo-1-methoxy-2-(methoxymethoxy)benzene

(2S,2aS,4R,4aS,5R,6R,7R,7aS,7bR)-5-tert-butyldimethylsiloxy-2-hydroxy-6,7-(O-isopropylidenedioxy)decahydroindeno[7,1-bc]furan-4-carbaldehyde

2-methoxyphenyl benzoate

5-bromo-2-methoxyphenol

Downstream raw materials:

C₂₉H₄₆O₈Si

(1R,3R,3aS,4S,5R,6R,7R,7aR)-4-acetoxy-3-acetoxymethyl-7-tert-butyldimethylsiloxy-1-[(1S)-acetoxy[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-5,6-(isopropylidenedioxy)octahydroindene

(1R,3R,3aS,4S,5R,6R,7R,7aR)-7-tert-butyldimethylsiloxy-1-[(1S)-hydroxy[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-3-hydroxymethyl-5,6-(isopropylidenedioxy)octahydroindene-4-ol

(1S,3R,3aS,4S,5R,6R,7R,7aR)-7-tert-butyldimethylsiloxy-3-hydroxymethyl-5,6-O-isopropylidenedioxy-1-[4-methoxy-3-(methoxymethoxy)benzyl]octahydroinden-4-ol

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