(3R,4S)-N-(tert-butoxycarbonyl)-4-amino-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-phenylpentane

Base Information

Chemical Name:(3R,4S)-N-(tert-butoxycarbonyl)-4-amino-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-phenylpentane
CAS No.:229981-31-1
Molecular Formula:C₂₂H₃₉NO₄Si
Molecular Weight:409.641
Hs Code.:

Synonyms:(3R,4S)-N-(tert-butoxycarbonyl)-4-amino-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-phenylpentane

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Chemical Property of (3R,4S)-N-(tert-butoxycarbonyl)-4-amino-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-phenylpentane

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Technology Process of (3R,4S)-N-(tert-butoxycarbonyl)-4-amino-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-phenylpentane

There total 4 articles about (3R,4S)-N-(tert-butoxycarbonyl)-4-amino-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-phenylpentane 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:

: 124915-64-6
(4S,5R)-5-ethenyl-4-phenylmethyloxazolidin-2-one

: 229981-31-1
(3R,4S)-N-(tert-butoxycarbonyl)-4-amino-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-phenylpentane

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / Et₃N, DMAP / tetrahydrofuran / 5.5 h / Ambient temperature

2: 76 percent / Cs₂CO₃ / methanol / 25 h / Ambient temperature

3: 90 percent / imidazole / dimethylformamide / 2 h

4: 1.) 9-BBN, 2.) NaOH, H₂O₂ / 1.) THF, hexane, room temperature, 20 h, 2.) EtOH, 50 deg C, 1 h

With 1H-imidazole; dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; caesium carbonate; triethylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo990200x

Reference yield:

: 99113-30-1
((1S,2R)-1-benzyl-2-hydroxybut-3-enyl)carbamic acid tert-butyl ester

: 229981-31-1
(3R,4S)-N-(tert-butoxycarbonyl)-4-amino-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-phenylpentane

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / imidazole / dimethylformamide / 2 h

2: 1.) 9-BBN, 2.) NaOH, H₂O₂ / 1.) THF, hexane, room temperature, 20 h, 2.) EtOH, 50 deg C, 1 h

With 1H-imidazole; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; In N,N-dimethyl-formamide;
DOI:10.1021/jo990200x

Reference yield:

: 229981-17-3
(4S,5R)-N-(tert-butyloxycarbonyl)-5-ethenyl-4-phenylmethyl oxazolidin-2-one

: 229981-31-1
(3R,4S)-N-(tert-butoxycarbonyl)-4-amino-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-phenylpentane

Guidance literature:: Multi-step reaction with 3 steps

1: 76 percent / Cs₂CO₃ / methanol / 25 h / Ambient temperature

2: 90 percent / imidazole / dimethylformamide / 2 h

3: 1.) 9-BBN, 2.) NaOH, H₂O₂ / 1.) THF, hexane, room temperature, 20 h, 2.) EtOH, 50 deg C, 1 h

With 1H-imidazole; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; caesium carbonate; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo990200x