(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

Base Information

Chemical Name:(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
CAS No.:653573-94-5
Molecular Formula:C₂₉H₄₀O₆SSi
Molecular Weight:544.784
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 6 articles about (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 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: 96.0%

: 463-71-8
thiophosgene

: 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

: 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

Guidance literature:: With dmap; In dichloromethane; 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

: 653573-94-5
(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

Guidance literature:: Multi-step reaction with 9 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

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:

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

: 653573-94-5
(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

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / aq. NaOH / propan-2-ol / 20 °C

2: 96 percent / DMAP / CH₂Cl₂ / 20 °C

With dmap; sodium hydroxide; In dichloromethane; isopropyl alcohol;
DOI:10.1055/s-2003-42114