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

Base Information

Chemical Name:(1S,3R,3aR,4R,5R,6R,7aS)-3-(3-acetoxy-4-methoxybenzyl)-4-tert-butyldimethylsiloxy-7-methylene-1-(vinyl)octahydroindene-5,6-diol
CAS No.:653573-93-4
Molecular Formula:C₂₈H₄₂O₆Si
Molecular Weight:502.723
Hs Code.:

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

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

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

There total 5 articles about (1S,3R,3aR,4R,5R,6R,7aS)-3-(3-acetoxy-4-methoxybenzyl)-4-tert-butyldimethylsiloxy-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: 90.0%

: 108-24-7
acetic anhydride

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

: 653573-93-4
(1S,3R,3aR,4R,5R,6R,7aS)-3-(3-acetoxy-4-methoxybenzyl)-4-tert-butyldimethylsiloxy-7-methylene-1-(vinyl)octahydroindene-5,6-diol

Guidance literature:: With sodium hydroxide; In isopropyl alcohol; at 20 ℃;
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

: 653573-93-4
(1S,3R,3aR,4R,5R,6R,7aS)-3-(3-acetoxy-4-methoxybenzyl)-4-tert-butyldimethylsiloxy-7-methylene-1-(vinyl)octahydroindene-5,6-diol

Guidance literature:: Multi-step reaction with 8 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

8.1: 90 percent / aq. NaOH / propan-2-ol / 20 °C

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

Reference yield:

: 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

: 653573-93-4
(1S,3R,3aR,4R,5R,6R,7aS)-3-(3-acetoxy-4-methoxybenzyl)-4-tert-butyldimethylsiloxy-7-methylene-1-(vinyl)octahydroindene-5,6-diol

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / t-BuOK / benzene

2: 76 percent / aq. TFA / tetrahydrofuran / 0 °C

3: 90 percent / aq. NaOH / propan-2-ol / 20 °C

With sodium hydroxide; potassium tert-butylate; trifluoroacetic acid; In tetrahydrofuran; isopropyl alcohol; benzene; 1: Wittig methylenation;
DOI:10.1055/s-2003-42114