(2S,5R)-1-(benzyloxycarbonyl)-5-[(methoxycarbonyl)methyl]proline tert-butyl ester

Base Information

Chemical Name:(2S,5R)-1-(benzyloxycarbonyl)-5-[(methoxycarbonyl)methyl]proline tert-butyl ester
CAS No.:182137-24-2
Molecular Formula:C₂₀H₂₇NO₆
Molecular Weight:377.437
Hs Code.:

Synonyms:(2S,5R)-1-(benzyloxycarbonyl)-5-[(methoxycarbonyl)methyl]proline tert-butyl ester

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Chemical Property of (2S,5R)-1-(benzyloxycarbonyl)-5-[(methoxycarbonyl)methyl]proline tert-butyl ester

Chemical Property:

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Technology Process of (2S,5R)-1-(benzyloxycarbonyl)-5-[(methoxycarbonyl)methyl]proline tert-butyl ester

There total 4 articles about (2S,5R)-1-(benzyloxycarbonyl)-5-[(methoxycarbonyl)methyl]proline tert-butyl 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:

: 81477-94-3
N-(diphenylmethylene)glycine tert-butyl ester

: 182137-24-2
(2S,5R)-1-(benzyloxycarbonyl)-5-[(methoxycarbonyl)methyl]proline tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: aq. KOH / O-allyl N-(9-anthracenylmethyl)cinchonidinium bromide / toluene; CH₂Cl₂ / 1 h / -40 °C

2.1: aq. citric acid / tetrahydrofuran / 4 h / 20 °C

2.2: DBU / tetrahydrofuran / 18 h / 60 °C

3.1: 85 percent / aq. K₂CO₃ / ethyl acetate / 1 h / 20 °C

With potassium hydroxide; potassium carbonate; citric acid; O-allyl N-(9-anthracenylmethyl)cinchonidinium bromide; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/ja0707097

Reference yield:

: 939387-21-0
7-tert-butyl (E)-(S)-1-methyl-6-(diphenylmethyleneamino)hept-3-enedioate

: 182137-24-2
(2S,5R)-1-(benzyloxycarbonyl)-5-[(methoxycarbonyl)methyl]proline tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: aq. citric acid / tetrahydrofuran / 4 h / 20 °C

1.2: DBU / tetrahydrofuran / 18 h / 60 °C

2.1: 85 percent / aq. K₂CO₃ / ethyl acetate / 1 h / 20 °C

With potassium carbonate; citric acid; In tetrahydrofuran; ethyl acetate;
DOI:10.1021/ja0707097

Reference yield:

: 90741-31-4
(S)-N-benzyl-5-thioxoproline tert-butyl ester

: 182137-24-2
(2S,5R)-1-(benzyloxycarbonyl)-5-[(methoxycarbonyl)methyl]proline tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 2.) Ph₃P, NMP / 1.) CH₃CN, 42 h, 2.) CH₂Cl₂, -5 deg C, 30 h.

2: 1.) H₂, 2.) K₂CO₃ / 1.) Pd/C / 1.) MeOH, 60 psi, 36 h, 2.) EtOAc, H₂O, 1 h

With 1-methyl-pyrrolidin-2-one; hydrogen; potassium carbonate; triphenylphosphine; palladium on activated charcoal;
DOI:10.1021/jo960759m