(1S,3R,3aR,4R,5R,6R,7aS)-4-tert-butyldimethylsiloxy-3-(3-hydroxy-4-methoxybenzyl)-7-methylene-1-(vinyl)octahydroindene-5,6-diol

Base Information

• Chemical Name: (1S,3R,3aR,4R,5R,6R,7aS)-4-tert-butyldimethylsiloxy-3-(3-hydroxy-4-methoxybenzyl)-7-methylene-1-(vinyl)octahydroindene-5,6-diol
• CAS No.: 653573-92-3
• Molecular Formula: C₂₆H₄₀O₅Si
• Molecular Weight: 460.686

Synonyms:(1S,3R,3aR,4R,5R,6R,7aS)-4-tert-butyldimethylsiloxy-3-(3-hydroxy-4-methoxybenzyl)-7-methylene-1-(vinyl)octahydroindene-5,6-diol

Chemical Property of (1S,3R,3aR,4R,5R,6R,7aS)-4-tert-butyldimethylsiloxy-3-(3-hydroxy-4-methoxybenzyl)-7-methylene-1-(vinyl)octahydroindene-5,6-diol

Chemical Property:

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Safty Information:

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Technology Process of (1S,3R,3aR,4R,5R,6R,7aS)-4-tert-butyldimethylsiloxy-3-(3-hydroxy-4-methoxybenzyl)-7-methylene-1-(vinyl)octahydroindene-5,6-diol

There total 7 articles about (1S,3R,3aR,4R,5R,6R,7aS)-4-tert-butyldimethylsiloxy-3-(3-hydroxy-4-methoxybenzyl)-7-methylene-1-(vinyl)octahydroindene-5,6-diol 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: 76.0%

(1S,3R,3aR,4R,5R,6R,7aS)-4-tert-butyldimethylsiloxy-5,6-isopropylidenedioxy-3-[4-methoxy-3-(methoxymethoxy)benzyl]-7-methylene-1-(vinyl)octahydroindene (653573-91-2) → (1S,3R,3aR,4R,5R,6R,7aS)-4-tert-butyldimethylsiloxy-3-(3-hydroxy-4-methoxybenzyl)-7-methylene-1-(vinyl)octahydroindene-5,6-diol (653573-92-3)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; at 0 ℃;

DOI:10.1055/s-2003-42114

Reference yield:

4-bromo-1-methoxy-2-(methoxymethoxy)benzene (623550-16-3) → (1S,3R,3aR,4R,5R,6R,7aS)-4-tert-butyldimethylsiloxy-3-(3-hydroxy-4-methoxybenzyl)-7-methylene-1-(vinyl)octahydroindene-5,6-diol (653573-92-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-BuLi / tetrahydrofuran / -78 °C

1.2: 100 percent / tetrahydrofuran / -78 °C

2.1: 100 percent / DMAP; pyridine / 20 °C

3.1: 87 percent / Li; NH₃ / tetrahydrofuran / -78 °C

4.1: 52 percent / DBU / toluene / 1.5 h / Heating

5.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

6.1: 88 percent / t-BuOK / benzene

7.1: 76 percent / aq. TFA / tetrahydrofuran / 0 °C

With pyridine; dmap; n-butyllithium; potassium tert-butylate; ammonia; lithium; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene; benzene; 5.1: Dess-Martin oxidation / 6.1: Wittig methylenation;

DOI:10.1055/s-2003-42114

Reference yield:

(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) → (1S,3R,3aR,4R,5R,6R,7aS)-4-tert-butyldimethylsiloxy-3-(3-hydroxy-4-methoxybenzyl)-7-methylene-1-(vinyl)octahydroindene-5,6-diol (653573-92-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 100 percent / DBU / tetrahydrofuran / 20 °C

2.1: n-BuLi / tetrahydrofuran / -78 °C

2.2: 100 percent / tetrahydrofuran / -78 °C

3.1: 100 percent / DMAP; pyridine / 20 °C

4.1: 87 percent / Li; NH₃ / tetrahydrofuran / -78 °C

5.1: 52 percent / DBU / toluene / 1.5 h / Heating

6.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

7.1: 88 percent / t-BuOK / benzene

8.1: 76 percent / aq. TFA / tetrahydrofuran / 0 °C

With pyridine; dmap; n-butyllithium; potassium tert-butylate; ammonia; lithium; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene; benzene; 6.1: Dess-Martin oxidation / 7.1: Wittig methylenation;

DOI:10.1055/s-2003-42114

upstream raw materials:

(1S,3R,3aR,4R,5R,6R,7aS)-4-tert-butyldimethylsiloxy-5,6-isopropylidenedioxy-3-[4-methoxy-3-(methoxymethoxy)benzyl]-7-methylene-1-(vinyl)octahydroindene

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

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

Downstream raw materials:

(1S,3R,3aR,4R,5R,6R,7aS)-3-(3-acetoxy-4-methoxybenzyl)-4-tert-butyldimethylsiloxy-7-methylene-1-(vinyl)octahydroindene-5,6-diol

(3aR,4R,4aR,5R,7S,7aS,8aR)-5-(3-acetoxy-4-methoxybenzyl)-4-tert-butyldimethylsiloxy-8-methylene-7-(vinyl)octahydroindeno[5,6-d,1,3]dioxol-2-thione

(1S,3R,3aR,4S,7aS)-3-(3-acetoxy-4-methoxybenzyl)-4-tert-butyldimethylsiloxy-7-methylene-1-vinyl-1,2,3,3a,7,7a-hexahydroindene

(1S,3R,3aR,4S,7aS)-3-(3-acetoxy-4-methoxybenzyl)-7-methylene-1-vinyl-1,2,3,3a,7,7a-hexahydroinden-4-ol

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