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

Base Information

Chemical Name:(1S,3R,3aR,4S,7aS)-3-(3-acetoxy-4-methoxybenzyl)-4-tert-butyldimethylsiloxy-7-methylene-1-vinyl-1,2,3,3a,7,7a-hexahydroindene
CAS No.:653573-95-6
Molecular Formula:C₂₈H₄₀O₄Si
Molecular Weight:468.709
Hs Code.:

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

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

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

There total 9 articles about (1S,3R,3aR,4S,7aS)-3-(3-acetoxy-4-methoxybenzyl)-4-tert-butyldimethylsiloxy-7-methylene-1-vinyl-1,2,3,3a,7,7a-hexahydroindene 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%

: 653573-94-5
(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

: 653573-95-6
(1S,3R,3aR,4S,7aS)-3-(3-acetoxy-4-methoxybenzyl)-4-tert-butyldimethylsiloxy-7-methylene-1-vinyl-1,2,3,3a,7,7a-hexahydroindene

Guidance literature:: With triethyl phosphite; Heating;
DOI:10.1055/s-2003-42114

Reference yield:

: 623550-16-3
4-bromo-1-methoxy-2-(methoxymethoxy)benzene

: 653573-95-6
(1S,3R,3aR,4S,7aS)-3-(3-acetoxy-4-methoxybenzyl)-4-tert-butyldimethylsiloxy-7-methylene-1-vinyl-1,2,3,3a,7,7a-hexahydroindene

Guidance literature:: Multi-step reaction with 10 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

9.1: 96 percent / DMAP / CH₂Cl₂ / 20 °C

10.1: 76 percent / (EtO)3P / Heating

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; triethyl phosphite; In tetrahydrofuran; dichloromethane; isopropyl alcohol; toluene; benzene; 5.1: Dess-Martin oxidation / 6.1: Wittig methylenation;
DOI:10.1055/s-2003-42114

Reference yield:

: 623550-08-3
(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

: 653573-95-6
(1S,3R,3aR,4S,7aS)-3-(3-acetoxy-4-methoxybenzyl)-4-tert-butyldimethylsiloxy-7-methylene-1-vinyl-1,2,3,3a,7,7a-hexahydroindene

Guidance literature:: Multi-step reaction with 11 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

9.1: 90 percent / aq. NaOH / propan-2-ol / 20 °C

10.1: 96 percent / DMAP / CH₂Cl₂ / 20 °C

11.1: 76 percent / (EtO)3P / Heating

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; triethyl phosphite; In tetrahydrofuran; dichloromethane; isopropyl alcohol; toluene; benzene; 6.1: Dess-Martin oxidation / 7.1: Wittig methylenation;
DOI:10.1055/s-2003-42114