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

Base Information

Chemical Name:(1S,3R,3aR,4R,5R,6R,7aS)-4-tert-butyldimethylsiloxy-5,6-isopropylidenedioxy-3-[4-methoxy-3-(methoxymethoxy)benzyl]-7-methylene-1-(vinyl)octahydroindene
CAS No.:653573-91-2
Molecular Formula:C₃₁H₄₈O₆Si
Molecular Weight:544.804
Hs Code.:

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

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

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

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

There total 3 articles about (1S,3R,3aR,4R,5R,6R,7aS)-4-tert-butyldimethylsiloxy-5,6-isopropylidenedioxy-3-[4-methoxy-3-(methoxymethoxy)benzyl]-7-methylene-1-(vinyl)octahydroindene 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: 88.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 653573-90-1
(1R,3R,3aR,4R,5R,6S,7aR)-4-tert-butyldimethylsiloxy-5,6-isopropylidenedioxy-3-[4-methoxy-3-(methoxymethoxy)benzyl]-7-oxooctahydroinden-1-carbaldehyde

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

Guidance literature:: With potassium tert-butylate; In benzene;
DOI:10.1055/s-2003-42114

Reference yield:

: 653573-85-4
(2S,2aS,4S,4aS,5R,6R,7R,7aS,7bR)-5-tert-butyldimethylsilyloxy-2-hydroxy-6,7-(isopropylidenedioxy)decahydroindeno[7,1-bc]furan-4-carbaldehyde

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

Guidance literature:: Multi-step reaction with 6 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

With pyridine; dmap; n-butyllithium; potassium tert-butylate; ammonia; lithium; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; toluene; benzene; 5.1: Dess-Martin oxidation / 6.1: Wittig methylenation;
DOI:10.1055/s-2003-42114

Reference yield:

: 653573-88-7
(2S,2aS,4R,4aR,5R,6R,7R,7aS,7bR)-5-tert-butyldimethylsiloxy-4-[4-methoxy-3-(methoxymethoxy)benzyl]-6,7-(isopropylidenedioxy)decahydroindeno[7,1-bc]furan-2-ol

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

Guidance literature:: Multi-step reaction with 3 steps

1: 52 percent / DBU / toluene / 1.5 h / Heating

2: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

3: 88 percent / t-BuOK / benzene

With potassium tert-butylate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; toluene; benzene; 2: Dess-Martin oxidation / 3: Wittig methylenation;
DOI:10.1055/s-2003-42114