Technology Process of (1S,3S,3aS,4S,5R,6R,7R,7aR)-7-tert-butyldimethylsiloxy-5,6-O-isopropylidenedioxy-1-[4-methoxy-3-(methoxymethoxy)benzyl]-4-methylene-3-(vinyl)octahydroindene
There total 14 articles about (1S,3S,3aS,4S,5R,6R,7R,7aR)-7-tert-butyldimethylsiloxy-5,6-O-isopropylidenedioxy-1-[4-methoxy-3-(methoxymethoxy)benzyl]-4-methylene-3-(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:
- Guidance literature:
-
Methyltriphenylphosphonium bromide;
With
potassium tert-butylate;
In
benzene;
for 4h;
Heating;
(1R,3R,3aR,4R,5R,6S,7R)-4-tert-butyldimethylsiloxy-5,6-O-isopropylidenedioxy-3-[4-methoxy-3-(methoxymethoxy)benzyl]-7-oxooctahydroindene-1-carbaldehyde;
In
benzene;
at 20 ℃;
DOI:10.1021/ol035443x
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 88 percent / iPr2NEt / CH2Cl2 / 4 h / 0 - 20 °C
2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
2.2: 80 percent / tetrahydrofuran; hexane / 1 h / -78 °C
3.1: 30 percent / DBU / toluene / 1.5 h / Heating
4.1: 96 percent / LiAlH4 / tetrahydrofuran / 0.02 h / 0 °C
5.1: 95 percent / DMAP; pyridine / 1 h / 20 °C
6.1: 98 percent / Li; liquid NH3 / tetrahydrofuran / 0.08 h / -78 °C
7.1: 80 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
8.1: t-BuOK / benzene / 4 h / Heating
8.2: 95 percent / benzene / 20 °C
With
pyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; potassium tert-butylate; ammonia; lithium; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; hexane; dichloromethane; toluene; benzene;
8.2: Wittig reaction;
DOI:10.1021/ol035443x
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: Br2; AcOH / 20 °C
2.1: K2CO3 / methanol / 20 °C
3.1: 88 percent / iPr2NEt / CH2Cl2 / 4 h / 0 - 20 °C
4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
4.2: 80 percent / tetrahydrofuran; hexane / 1 h / -78 °C
5.1: 30 percent / DBU / toluene / 1.5 h / Heating
6.1: 96 percent / LiAlH4 / tetrahydrofuran / 0.02 h / 0 °C
7.1: 95 percent / DMAP; pyridine / 1 h / 20 °C
8.1: 98 percent / Li; liquid NH3 / tetrahydrofuran / 0.08 h / -78 °C
9.1: 80 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
10.1: t-BuOK / benzene / 4 h / Heating
10.2: 95 percent / benzene / 20 °C
With
pyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; potassium tert-butylate; ammonia; bromine; lithium; potassium carbonate; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; hexane; dichloromethane; toluene; benzene;
10.2: Wittig reaction;
DOI:10.1021/ol035443x
