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

Base Information

Chemical Name:(1R,3R,3aR,4R,5R,6R,7S,7aR)-4-tert-butyldimethylsiloxy-7-hydroxy-3-[(1S)-hydroxy[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-5,6-(isopropylidenedioxy)octahydroindene-1-carbaldehyde
CAS No.:623550-22-1
Molecular Formula:C₂₉H₄₆O₉Si
Molecular Weight:566.764
Hs Code.:

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

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

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Chemical Property of (1R,3R,3aR,4R,5R,6R,7S,7aR)-4-tert-butyldimethylsiloxy-7-hydroxy-3-[(1S)-hydroxy[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-5,6-(isopropylidenedioxy)octahydroindene-1-carbaldehyde

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Technology Process of (1R,3R,3aR,4R,5R,6R,7S,7aR)-4-tert-butyldimethylsiloxy-7-hydroxy-3-[(1S)-hydroxy[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-5,6-(isopropylidenedioxy)octahydroindene-1-carbaldehyde

There total 8 articles about (1R,3R,3aR,4R,5R,6R,7S,7aR)-4-tert-butyldimethylsiloxy-7-hydroxy-3-[(1S)-hydroxy[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-5,6-(isopropylidenedioxy)octahydroindene-1-carbaldehyde 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: 30.0%

: 623550-19-6
(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

: 623550-22-1
(1R,3R,3aR,4R,5R,6R,7S,7aR)-4-tert-butyldimethylsiloxy-7-hydroxy-3-[(1S)-hydroxy[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-5,6-(isopropylidenedioxy)octahydroindene-1-carbaldehyde

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 1.5h; Heating;
DOI:10.1021/ol035443x DOI:10.1002/chem.200700789

Reference yield:

: 37942-01-1
5-bromo-2-methoxyphenol

: 623550-22-1
(1R,3R,3aR,4R,5R,6R,7S,7aR)-4-tert-butyldimethylsiloxy-7-hydroxy-3-[(1S)-hydroxy[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-5,6-(isopropylidenedioxy)octahydroindene-1-carbaldehyde

Guidance literature:: Multi-step reaction with 3 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

3.1: 30 percent / DBU / toluene / 1.5 h / Heating

With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1021/ol035443x

Reference yield:

: 531-37-3
2-methoxyphenyl benzoate

: 623550-22-1
(1R,3R,3aR,4R,5R,6R,7S,7aR)-4-tert-butyldimethylsiloxy-7-hydroxy-3-[(1S)-hydroxy[4-methoxy-3-(methoxymethoxy)phenyl]methyl]-5,6-(isopropylidenedioxy)octahydroindene-1-carbaldehyde

Guidance literature:: Multi-step reaction with 5 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

5.1: 30 percent / DBU / toluene / 1.5 h / Heating

With n-butyllithium; bromine; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;
DOI:10.1021/ol035443x