(3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester

Base Information

Chemical Name:(3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester
CAS No.:366498-33-1
Molecular Formula:C₂₀H₂₇NO₄
Molecular Weight:345.439
Hs Code.:

Synonyms:(3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester

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Chemical Property of (3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester

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Technology Process of (3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester

There total 4 articles about (3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-L-proline methyl 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: 85.7%

: 590-15-8
trans-2-propenyl bromide

: 366498-36-4
(3S)-N-tert-butyloxycarbonyl-5-methoxy-3-phenyl-L-proline methyl ester

: 366498-33-1
(3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester

Guidance literature:: trans-2-propenyl bromide; With lithium; In diethyl ether; at -20 ℃; for 2h;

With copper(I) bromide dimethylsulfide complex; In diethyl ether; at -40 ℃; for 1h;

(3S)-N-tert-butyloxycarbonyl-5-methoxy-3-phenyl-L-proline methyl ester; With boron trifluoride diethyl etherate; In diethyl ether; for 0.25h;
DOI:10.1016/S0040-4020(01)00532-4

Reference yield:

: 366498-31-9
methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate

: 366498-33-1
(3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: BF₃*THF / tetrahydrofuran / 0 - 20 °C

1.2: MCPBA / tetrahydrofuran / 0 - 20 °C

1.3: 70 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 90 mg / PPTS / 24 h / 20 °C

3.1: Li / diethyl ether / 2 h / -20 °C

3.2: CuBr*Me₂S / diethyl ether / 1 h / -40 °C

3.3: 85.7 percent / BF₃*Et₂O / diethyl ether / 0.25 h

With boron trifluoride-tetrahydrofuran complex; pyridinium p-toluenesulfonate; lithium; In tetrahydrofuran; diethyl ether; 1.3: Swern oxidation;
DOI:10.1016/S0040-4020(01)00532-4

Reference yield:

: 366498-32-0
(3S)-N-tert-butyloxycarbonyl-5-hydroxy-3-phenyl-L-proline methyl ester

: 366498-33-1
(3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 90 mg / PPTS / 24 h / 20 °C

2.1: Li / diethyl ether / 2 h / -20 °C

2.2: CuBr*Me₂S / diethyl ether / 1 h / -40 °C

2.3: 85.7 percent / BF₃*Et₂O / diethyl ether / 0.25 h

With pyridinium p-toluenesulfonate; lithium; In diethyl ether;
DOI:10.1016/S0040-4020(01)00532-4