Fmoc-3,4-dehydro-L-proline

Base Information

• Chemical Name: Fmoc-3,4-dehydro-L-proline
• CAS No.: 135837-63-7
• Molecular Formula: C20H17 N O4
• Molecular Weight: 335.35
• Hs Code.: 2933 99 80
• DSSTox Substance ID: DTXSID90474519
• Wikidata: Q72478592
• Mol file: 135837-63-7.mol

Synonyms:135837-63-7;Fmoc-3,4-dehydroPro-OH;Fmoc-3,4-dehydro-L-proline;(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid;(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)-2,5-dihydropyrrole-2-carboxylic Acid;Fmoc-deltaPro-OH;Fmoc-delta-Pro-OH;SCHEMBL12964290;DTXSID90474519;MFCD00151940;AKOS025312286;HY-W053705;AS-46820;Fmoc-3,4-dehydro-L-proline, AldrichCPR;PD197228;CS-0046773;F10621;N-alpha-(9-Fluorenylmethyloxycarbonyl)-3,4-dehydro-L-proline;1H-Pyrrole-1,2-dicarboxylicacid,2,5-dihydro-,1-(9H-fluoren-9-ylmethyl)ester,(2S)-

Chemical Property of Fmoc-3,4-dehydro-L-proline

Chemical Property:

• Boiling Point: 549.6±50.0 °C(Predicted)
• PKA: 3?+-.0.20(Predicted)
• PSA: 66.84000
• Density: 1.356±0.06 g/cm3(Predicted)
• LogP: 3.19840
• Storage Temp.: -15°C
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 335.11575802
• Heavy Atom Count: 25
• Complexity: 538

Purity/Quality:

98%min ^*data from raw suppliers

Fmoc-3,4-dehydro-L-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CC(N1C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)O
• Isomeric SMILES: C1C=C[C@H](N1C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)O

Technology Process of Fmoc-3,4-dehydro-L-proline

There total 7 articles about Fmoc-3,4-dehydro-L-proline 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: 76.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 3,4-dehydro-L-proline trifluoroacetate salt → 3,4-dehydro-1-(9-fluorenylmethoxycarbonyl)-L-proline (135837-63-7)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; at 25 ℃; for 4h;

DOI:10.1016/j.ejmech.2016.04.001

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 3,4-dehydro-L-proline (4043-88-3,58640-72-5) → 3,4-dehydro-1-(9-fluorenylmethoxycarbonyl)-L-proline (135837-63-7)

Guidance literature:

In acetonitrile; at 30 ℃; for 0.166667h;

DOI:10.1021/acs.oprd.1c00405

Reference yield:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → 3,4-dehydro-1-(9-fluorenylmethoxycarbonyl)-L-proline (135837-63-7)

Guidance literature:

Multi-step reaction with 5 steps

1: methyl iodide; di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 4 h / 0 - 25 °C / Inert atmosphere

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 15 h / 25 - 85 °C / Inert atmosphere

3: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 25 °C / Inert atmosphere

4: dichloromethane / 2 h / 25 °C / Inert atmosphere

5: sodium carbonate / 1,4-dioxane / 4 h / 25 °C

With di-isopropyl azodicarboxylate; water; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; lithium hydroxide; methyl iodide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene; 1: |Mitsunobu Displacement;

DOI:10.1016/j.ejmech.2016.04.001

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

3,4-dehydro-L-proline

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

(2S,4S)-2-methyl 1-tert-butyl 4-iodopyrrolidine-1,2-dicarboxylate

Downstream raw materials:

C₃₉H₆₄N₁₂O₈

Refernces

• 1、 Dussauge, Solene,Moore, Charles,Snajdrova, Radka,Tassano, Erika,Vargas, Alexandra. "Discovery of New Fe(II)/α-Ketoglutarate-Dependent Dioxygenases for Oxidation of l-Proline". supporting information. . Retrieved 2022/02/09.