Technology Process of (-)-(RS,2S,3R,4R,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide
There total 5 articles about (-)-(RS,2S,3R,4R,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(methoxymethyl)[(3-trimethylsilyl)prop-2-ynyl]ether;
With
tert.-butyl lithium;
In
tetrahydrofuran; pentane;
at -95 ℃;
for 1h;
Inert atmosphere;
With
N,N,N,N,N,N-hexamethylphosphoric triamide; copper(I) cyanide di(lithium chloride);
In
tetrahydrofuran; pentane;
at -95 - -80 ℃;
for 0.0833333h;
Inert atmosphere;
(1)-(RS,E,2S,3R)-N-[2,3-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)butylidene]-2-methylpropane-1-sulfinamide;
In
tetrahydrofuran; pentane;
at -80 ℃;
for 1h;
diastereoselective reaction;
Inert atmosphere;
DOI:10.1021/ol202747p
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: calcium sulfate; silver(l) oxide / acetonitrile / 48 h / 20 °C / Darkness
2.1: trimethylaluminum / tetrahydrofuran; toluene / 0.5 h / 0 - 20 °C
2.2: 17 h / -15 - 20 °C
3.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 0 °C
4.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.5 h / -80 - -78 °C / Inert atmosphere
5.1: titanium(IV) tetraethanolate / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere
6.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -95 °C / Inert atmosphere
6.2: 0.08 h / -95 - -80 °C / Inert atmosphere
6.3: 1 h / -80 °C / Inert atmosphere
With
1H-imidazole; titanium(IV) tetraethanolate; calcium sulfate; trimethylaluminum; tert.-butyl lithium; diisobutylaluminium hydride; silver(l) oxide;
In
tetrahydrofuran; N,N-dimethyl-formamide; toluene; acetonitrile; pentane;
DOI:10.1021/ol202747p
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: trimethylaluminum / tetrahydrofuran; toluene / 0.5 h / 0 - 20 °C
1.2: 17 h / -15 - 20 °C
2.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 0 °C
3.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.5 h / -80 - -78 °C / Inert atmosphere
4.1: titanium(IV) tetraethanolate / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere
5.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -95 °C / Inert atmosphere
5.2: 0.08 h / -95 - -80 °C / Inert atmosphere
5.3: 1 h / -80 °C / Inert atmosphere
With
1H-imidazole; titanium(IV) tetraethanolate; trimethylaluminum; tert.-butyl lithium; diisobutylaluminium hydride;
In
tetrahydrofuran; N,N-dimethyl-formamide; toluene; pentane;
DOI:10.1021/ol202747p
![<sup>(1)</sup>-(RS,E,2S,3R)-N-[2,3-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)butylidene]-2-methylpropane-1-sulfinamide](/Databaselist/images/loading.webp)
