3-(4-((R)-((3R,6S)-6-(1H-indol-3-yl)-5-oxomorpholin-3-yl)((tert-butyldimethylsilyl)oxy)methyl)phenoxy)propanenitrile

Base Information

• Chemical Name: 3-(4-((R)-((3R,6S)-6-(1H-indol-3-yl)-5-oxomorpholin-3-yl)((tert-butyldimethylsilyl)oxy)methyl)phenoxy)propanenitrile
• CAS No.: 1350705-88-2
• Molecular Formula: C₂₈H₃₅N₃O₄Si
• Molecular Weight: 505.689

Synonyms:3-(4-((R)-((3R,6S)-6-(1H-indol-3-yl)-5-oxomorpholin-3-yl)((tert-butyldimethylsilyl)oxy)methyl)phenoxy)propanenitrile

Chemical Property of 3-(4-((R)-((3R,6S)-6-(1H-indol-3-yl)-5-oxomorpholin-3-yl)((tert-butyldimethylsilyl)oxy)methyl)phenoxy)propanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(4-((R)-((3R,6S)-6-(1H-indol-3-yl)-5-oxomorpholin-3-yl)((tert-butyldimethylsilyl)oxy)methyl)phenoxy)propanenitrile

There total 13 articles about 3-(4-((R)-((3R,6S)-6-(1H-indol-3-yl)-5-oxomorpholin-3-yl)((tert-butyldimethylsilyl)oxy)methyl)phenoxy)propanenitrile 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:

indole (120-72-9) → 3-(4-((R)-((3R,6S)-6-(1H-indol-3-yl)-5-oxomorpholin-3-yl)((tert-butyldimethylsilyl)oxy)methyl)phenoxy)propanenitrile (1350705-88-2)

Guidance literature:

Multi-step reaction with 4 steps

1: diethyl ether / 0.5 h / 0 °C / Inert atmosphere

2: triethylamine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

3: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere

4: pyridinium p-toluenesulfonate / acetonitrile / 1 h / Inert atmosphere; Reflux

With sodium tetrahydroborate; pyridinium p-toluenesulfonate; triethylamine; In methanol; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1039/c1ob06320k

Reference yield:

ethyl (2S,3R)-3-(4-(benzyloxy)phenyl)-2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate (1350705-68-8) → 3-(4-((R)-((3R,6S)-6-(1H-indol-3-yl)-5-oxomorpholin-3-yl)((tert-butyldimethylsilyl)oxy)methyl)phenoxy)propanenitrile (1350705-88-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

2: 5%-palladium/activated carbon; hydrogen / methanol / 12 h / 20 °C / Inert atmosphere

3: N-benzyl-trimethylammonium hydroxide / 8 h / Reflux; Inert atmosphere

4: lithium borohydride / methanol; diethyl ether / 4 h / 20 °C / Inert atmosphere

5: ytterbium(III) triflate / dichloromethane / 8 h / Inert atmosphere; Reflux

6: triethylamine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

7: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere

8: pyridinium p-toluenesulfonate / acetonitrile / 1 h / Inert atmosphere; Reflux

With 1H-imidazole; sodium tetrahydroborate; lithium borohydride; 5%-palladium/activated carbon; hydrogen; pyridinium p-toluenesulfonate; N-benzyl-trimethylammonium hydroxide; triethylamine; ytterbium(III) triflate; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3: Michael reaction;

DOI:10.1039/c1ob06320k

Reference yield:

p-benzyloxybenzaldehyde (4397-53-9) → 3-(4-((R)-((3R,6S)-6-(1H-indol-3-yl)-5-oxomorpholin-3-yl)((tert-butyldimethylsilyl)oxy)methyl)phenoxy)propanenitrile (1350705-88-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: water / 2 h / 90 °C / Inert atmosphere

2.1: tert-butylhypochlorite; sodium hydroxide / propan-1-ol; water / 0.08 h / Inert atmosphere

2.2: 2 h / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

4.1: 5%-palladium/activated carbon; hydrogen / methanol / 12 h / 20 °C / Inert atmosphere

5.1: N-benzyl-trimethylammonium hydroxide / 8 h / Reflux; Inert atmosphere

6.1: lithium borohydride / methanol; diethyl ether / 4 h / 20 °C / Inert atmosphere

7.1: ytterbium(III) triflate / dichloromethane / 8 h / Inert atmosphere; Reflux

8.1: triethylamine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

9.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere

10.1: pyridinium p-toluenesulfonate / acetonitrile / 1 h / Inert atmosphere; Reflux

With 1H-imidazole; sodium tetrahydroborate; lithium borohydride; tert-butylhypochlorite; 5%-palladium/activated carbon; hydrogen; pyridinium p-toluenesulfonate; N-benzyl-trimethylammonium hydroxide; triethylamine; sodium hydroxide; ytterbium(III) triflate; In methanol; propan-1-ol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 5.1: Michael reaction;

DOI:10.1039/c1ob06320k

upstream raw materials:

indole

p-benzyloxybenzaldehyde

C₁₈H₃₀N₂O₃Si

ethyl (2S,3R)-3-(4-(benzyloxy)phenyl)-2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate

Downstream raw materials:

oxazinin-6

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