Fmoc-4,5-didehydro-DL-leucine

Base Information

• Chemical Name: Fmoc-4,5-didehydro-DL-leucine
• CAS No.: 131177-58-7
• Molecular Formula: C₂₁H₂₁NO₄
• Molecular Weight: 351.402
• Mol file: 131177-58-7.mol

Synonyms:Fmoc-4,5-didehydro-DL-leucine

Chemical Property of Fmoc-4,5-didehydro-DL-leucine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Fmoc-4,5-didehydro-DL-leucine

There total 2 articles about Fmoc-4,5-didehydro-DL-leucine 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: 91.6%

DL-γ,δ-didehydroleucine (28024-78-4,905929-81-9) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → Fmoc-4,5-didehydro-DL-leucine (131177-58-7,917099-00-4)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; 1) 1 h, 0 deg C, 2) 3 h, RT;

Reference yield:

C6H11NO2*H(1+) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Fmoc-4,5-didehydro-DL-leucine (131177-58-7,917099-00-4)

Guidance literature:

With sodium carbonate;

DOI:10.1002/anie.201602806

Reference yield:

Fmoc-4,5-didehydro-DL-leucine (131177-58-7,917099-00-4) → D-Ala2-Leu5-enkephalin (60284-47-1,63631-40-3,64963-01-5,64963-05-9,64963-08-2,64975-66-2)

Guidance literature:

Multi-step reaction with 3 steps

1: N,N'-dicyclohexylcarbodi-imide / CH₂Cl₂; dimethylformamide / 1) 1 h, 0 deg C, 2) 1 h, RT

2: p-Benzyloxybenzyl alcohol resin

3: H₂ / Pd black / methanol / 2 h

With p-Benzyloxybenzyl alcohol resin; hydrogen; dicyclohexyl-carbodiimide; palladium; In methanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

DL-γ,δ-didehydroleucine

(fluorenylmethoxy)carbonyl chloride

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

Downstream raw materials:

(R)-2-[(S)-2-(2-{(R)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-propionylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid

D-Ala₂-Leu₅-enkephalin

2,4,5-didehydro-D-Leu⁵>Leu-enkephalin

2,4,5-didehydro-L-Leu⁵>Leu-enkephalin

Refernces

• 1、 Hasegawa, Hiroshi,Shinohara, Yoshihiko,Baba, Shigeo. "Synthesis of 2>Leu-enkephalin and 2,D-Leu5>Leu-enkephalin with High Specific Tritiated Activity in the Leucine Residue". . p. 2641 - 2644. Retrieved 2007/10/02.