(2R,3S,E)-3-(N-benzyl-N-t-butoxycarbonyl)amino-2-<(S)-1-(t-butyldimethylsiloxy)ethyl>-5-phenyl-4-pentenoic acid

Base Information

Chemical Name:(2R,3S,E)-3-(N-benzyl-N-t-butoxycarbonyl)amino-2-<(S)-1-(t-butyldimethylsiloxy)ethyl>-5-phenyl-4-pentenoic acid
CAS No.:142039-71-2
Molecular Formula:C₃₁H₄₅NO₅Si
Molecular Weight:539.788
Hs Code.:

Synonyms:(2R,3S,E)-3-(N-benzyl-N-t-butoxycarbonyl)amino-2-<(S)-1-(t-butyldimethylsiloxy)ethyl>-5-phenyl-4-pentenoic acid

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Chemical Property of (2R,3S,E)-3-(N-benzyl-N-t-butoxycarbonyl)amino-2-<(S)-1-(t-butyldimethylsiloxy)ethyl>-5-phenyl-4-pentenoic acid

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Technology Process of (2R,3S,E)-3-(N-benzyl-N-t-butoxycarbonyl)amino-2-<(S)-1-(t-butyldimethylsiloxy)ethyl>-5-phenyl-4-pentenoic acid

There total 13 articles about (2R,3S,E)-3-(N-benzyl-N-t-butoxycarbonyl)amino-2-<(S)-1-(t-butyldimethylsiloxy)ethyl>-5-phenyl-4-pentenoic acid 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: 89.0%

: 142039-70-1
Benzyl-[(1S,2S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-formyl-1-((E)-styryl)-butyl]-carbamic acid tert-butyl ester

: 142039-71-2
(2R,3S,E)-3-(N-benzyl-N-t-butoxycarbonyl)amino-2-<(S)-1-(t-butyldimethylsiloxy)ethyl>-5-phenyl-4-pentenoic acid

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol; for 1.5h; Ambient temperature;
DOI:10.1246/bcsj.68.2103

Reference yield:

: 142065-10-9
Benzyl-[(1S,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-1-((E)-styryl)-2-triethylsilanyloxymethyl-butyl]-amine

: 142039-71-2
(2R,3S,E)-3-(N-benzyl-N-t-butoxycarbonyl)amino-2-<(S)-1-(t-butyldimethylsiloxy)ethyl>-5-phenyl-4-pentenoic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 61 percent / Et₃N / dimethylformamide / 4.5 h / 50 °C

2: 98 percent / aq. AcOH / tetrahydrofuran / 72 h

3: 82 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h / -45 °C

4: 89 percent / aq. NaClO₂, NaH₂PO₄*2H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol / 1.5 h / Ambient temperature

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1246/bcsj.68.2103

Reference yield:

: 142065-12-1
t-butyl (1S,2R,3S)-N-benzyl-N-<3-t-butyldimethylsiloxy-1-(E)-styryl-2-(triethylsiloxy)methylbutyl>carbamate

: 142039-71-2
(2R,3S,E)-3-(N-benzyl-N-t-butoxycarbonyl)amino-2-<(S)-1-(t-butyldimethylsiloxy)ethyl>-5-phenyl-4-pentenoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 98 percent / aq. AcOH / tetrahydrofuran / 72 h

2: 82 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h / -45 °C

3: 89 percent / aq. NaClO₂, NaH₂PO₄*2H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol / 1.5 h / Ambient temperature

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; acetic acid; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;
DOI:10.1246/bcsj.68.2103