(S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-(diethylphosphono)-2-naphthalenecarboxylic acid benzyl ester

Base Information

Chemical Name:(S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-(diethylphosphono)-2-naphthalenecarboxylic acid benzyl ester
CAS No.:690254-50-3
Molecular Formula:C₂₇H₃₆NO₇P
Molecular Weight:517.559
Hs Code.:

Synonyms:(S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-(diethylphosphono)-2-naphthalenecarboxylic acid benzyl ester

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Chemical Property of (S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-(diethylphosphono)-2-naphthalenecarboxylic acid benzyl ester

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Technology Process of (S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-(diethylphosphono)-2-naphthalenecarboxylic acid benzyl ester

There total 4 articles about (S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-(diethylphosphono)-2-naphthalenecarboxylic acid benzyl ester 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: 93.0%

: 762-04-9
phosphonic acid diethyl ester

: 690254-49-0
benzyl (S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-bromo-2-naphthalenecarboxylate

: 690254-50-3
(S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-(diethylphosphono)-2-naphthalenecarboxylic acid benzyl ester

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In toluene; at 90 ℃;
DOI:10.1016/j.tet.2004.02.005

Reference yield:

: 4133-35-1
6-bromo-2-tetralone

: 690254-50-3
(S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-(diethylphosphono)-2-naphthalenecarboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 81 percent / (NH₄)2CO₃ / aq. ethanol / 1 h / Heating

2.1: 95 percent / Ba(OH)2 / H₂O / 36 h / Heating

3.1: 57 percent / SOCl₂ / 3 h / Heating

4.1: L-(+)-mandelic acid / diethyl ether; methanol

4.2: 35 mg / Et₃N / CHCl₃ / 48 h / 20 °C

5.1: 98 percent / aq. LiOH / tetrahydrofuran / 0 - 20 °C

6.1: 97 percent / iPr₂EtN / dimethylformamide / 24 h / 20 °C

7.1: 93 percent / Et₃N; Pd(PPh₃)4 / toluene / 90 °C

With barium dihydroxide; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; (S)-Mandelic acid; ammonium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2004.02.005

Reference yield:

: 690254-43-4
methyl 2-amino-1,2,3,4-tetrahydro-6-bromo-2-naphthalenecarboxylate

: 690254-50-3
(S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-(diethylphosphono)-2-naphthalenecarboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: L-(+)-mandelic acid / diethyl ether; methanol

1.2: 35 mg / Et₃N / CHCl₃ / 48 h / 20 °C

2.1: 98 percent / aq. LiOH / tetrahydrofuran / 0 - 20 °C

3.1: 97 percent / iPr₂EtN / dimethylformamide / 24 h / 20 °C

4.1: 93 percent / Et₃N; Pd(PPh₃)4 / toluene / 90 °C

With lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; (S)-Mandelic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2004.02.005