(2R)-N-(benzyloxycarbonyl)-2-[(E)-3'-(carbomethoxy)prop-2'-enyl]proline methyl ester

Base Information

• Chemical Name: (2R)-N-(benzyloxycarbonyl)-2-[(E)-3'-(carbomethoxy)prop-2'-enyl]proline methyl ester
• CAS No.: 325460-62-6
• Molecular Formula: C₁₉H₂₃NO₆
• Molecular Weight: 361.395
• Mol file: 325460-62-6.mol

Synonyms:(2R)-N-(benzyloxycarbonyl)-2-[(E)-3'-(carbomethoxy)prop-2'-enyl]proline methyl ester

Chemical Property of (2R)-N-(benzyloxycarbonyl)-2-[(E)-3'-(carbomethoxy)prop-2'-enyl]proline methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-N-(benzyloxycarbonyl)-2-[(E)-3'-(carbomethoxy)prop-2'-enyl]proline methyl ester

There total 1 articles about (2R)-N-(benzyloxycarbonyl)-2-[(E)-3'-(carbomethoxy)prop-2'-enyl]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:

(R)-N-(benzoyloxycarbonyl)-allylproline methyl ester (157662-40-3) → (2R)-N-(benzyloxycarbonyl)-2-[(E)-3'-(carbomethoxy)prop-2'-enyl]proline methyl ester (325460-62-6)

Guidance literature:

Multi-step reaction with 2 steps

1: O₃ / CH₂Cl₂ / 1.25 h / -78 °C

2: 9.96 g / CH₂Cl₂ / -78 - 20 °C

With ozone; In dichloromethane; 1: ozonolysis / 2: Wittig reaction;

DOI:10.1016/S0040-4020(00)00886-3

Reference yield: 61.0%

(2R)-N-(benzyloxycarbonyl)-2-[(E)-3'-(carbomethoxy)prop-2'-enyl]proline methyl ester (325460-62-6) → (R)-6-Oxo-8-phenyl-1-aza-spiro[4.4]nonane-1,7-dicarboxylic acid 1-benzyl ester 7-methyl ester + (2R)-N-(benzyloxycarbonyl)-2-[2'-(phenyl)-3'-(carbomethoxy)-propyl]proline methyl ester (325460-63-7)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; at -78 - -20 ℃;

DOI:10.1016/S0040-4020(00)00886-3

Reference yield:

(2R)-N-(benzyloxycarbonyl)-2-[(E)-3'-(carbomethoxy)prop-2'-enyl]proline methyl ester (325460-62-6) → (6R)-1-aza-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]nonane (325460-75-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 61 percent / BF₃*Et₂O / diethyl ether; tetrahydrofuran / -78 - -20 °C

2: H₂ / Pd/BaSO₄ / methanol

3: 2.4 g / Et₃N / toluene / 21 h / Heating

4: 93 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

With lithium borohydride; boron trifluoride diethyl etherate; hydrogen; triethylamine; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; toluene; 1: Addition / 2: Hydrogenolysis / 3: cyclocondensation / 4: Reduction;

DOI:10.1016/S0040-4020(00)00886-3

upstream raw materials:

(R)-N-(benzoyloxycarbonyl)-allylproline methyl ester

Downstream raw materials:

(2R)-N-(benzyloxycarbonyl)-2-[2'-(phenyl)-3'-(carbomethoxy)-propyl]proline methyl ester

(6R)-1-aza-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]nonane

(6R)-1-aza-6-carbomethoxy-4-phenyl-2-oxobicyclo[4.3.0]nonane

(2R)-2-[2'-(phenyl)-3'-(carbomethoxy)-propyl]proline methyl ester