tert-butyl (1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxypropan-2-ylcarbamate

Base Information

Chemical Name:tert-butyl (1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxypropan-2-ylcarbamate
CAS No.:1350705-70-2
Molecular Formula:C₂₃H₃₈N₂O₅Si
Molecular Weight:450.651
Hs Code.:

Synonyms:tert-butyl (1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxypropan-2-ylcarbamate

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Chemical Property of tert-butyl (1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxypropan-2-ylcarbamate

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Technology Process of tert-butyl (1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxypropan-2-ylcarbamate

There total 7 articles about tert-butyl (1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxypropan-2-ylcarbamate 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: 83.0%

: 1350705-83-7
ethyl (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)-3-(4-(2-cyanoethoxy)phenyl)propanoate

: 1350705-70-2
tert-butyl (1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxypropan-2-ylcarbamate

Guidance literature:: With lithium borohydride; In methanol; diethyl ether; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1039/c1ob06320k

Reference yield:

: 4397-53-9
p-benzyloxybenzaldehyde

: 1350705-70-2
tert-butyl (1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxypropan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; lithium borohydride; tert-butylhypochlorite; 5%-palladium/activated carbon; hydrogen; N-benzyl-trimethylammonium hydroxide; sodium hydroxide; In methanol; propan-1-ol; diethyl ether; water; N,N-dimethyl-formamide; 5.1: Michael reaction;
DOI:10.1039/c1ob06320k

Reference yield:

: 1350705-81-5
(2S,3R)-ethyl 3-(4-(benzyloxy)phenyl)-2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate

: 1350705-70-2
tert-butyl (1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxypropan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 3 steps

1: 5%-palladium/activated carbon; hydrogen / methanol / 12 h / 20 °C / Inert atmosphere

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

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

With lithium borohydride; 5%-palladium/activated carbon; hydrogen; N-benzyl-trimethylammonium hydroxide; In methanol; diethyl ether; 2: Michael reaction;
DOI:10.1039/c1ob06320k