Fmoc-4,5-dehydro-D-Leucine

Base Information

• Chemical Name: Fmoc-4,5-dehydro-D-Leucine
• CAS No.: 917099-00-4
• Molecular Formula: C₂₁H₂₁NO₄
• Molecular Weight: 351.402
• Hs Code.: 29225090
• DSSTox Substance ID: DTXSID00373221
• Wikidata: Q82161389
• Mol file: 917099-00-4.mol

Synonyms:917099-00-4;Fmoc-4,5-dehydro-D-Leucine;Fmoc-4,5-dehydro-D-Leu-OH;Fmoc-(R)-2-methallylglycine;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylpent-4-enoic acid;4-Pentenoicacid, 2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-methyl-, (2R)-;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-methylpent-4-enoic acid;Fmoc-4,5-dehydro-Leu-OH;SCHEMBL800126;DTXSID00373221;MFCD04112681;AKOS025295915;AS-81981;CS-0321832;A50371;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-methylpent-4-enoic acid;4-Pentenoicacid,2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-methyl-,(2R)-

Chemical Property of Fmoc-4,5-dehydro-D-Leucine

Chemical Property:

• PSA: 79.12000
• LogP: 4.14890
• Storage Temp.: Store at?0-5°C
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 351.14705815
• Heavy Atom Count: 26
• Complexity: 524

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-4,5-dehydro-d-leu-oh ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)CC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(=C)C[C@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Technology Process of Fmoc-4,5-dehydro-D-Leucine

There total 4 articles about Fmoc-4,5-dehydro-D-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: 90.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (2S)-2-amino-4-methylpent-4-enoic acid (87392-13-0,905929-81-9) → N-fluoren-9-ylmethyloxycarbonyl-4,5-dehydro-L-leucine (87720-55-6,917099-00-4)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; at 20 ℃; for 2h;

DOI:10.1039/P19830000723

Reference yield: 32.0%

(R,S)-2-acetamido-4-methyl-4-pentenoic acid (87325-65-3,88547-24-4) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → N-fluoren-9-ylmethyloxycarbonyl-4,5-dehydro-L-leucine (87720-55-6,917099-00-4)

Guidance literature:

(R,S)-2-acetamido-4-methyl-4-pentenoic acid; With ammonium hydroxide; In water; at 33 ℃; for 24h; pH=7.2; Enzymatic reaction;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; With sodium hydrogencarbonate; In water; at 20 ℃; for 5h;

DOI:10.1002/chem.201901888

upstream raw materials:

DL-γ,δ-didehydroleucine

(fluorenylmethoxy)carbonyl chloride

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

(2S)-2-amino-4-methylpent-4-enoic acid

Refernces

• 1、 Hu, Kuan,Geng, Hao,Zhang, Qingzhou,Liu, Qisong,Xie, Mingsheng,Sun, Chengjie,Li, Wenjun,Lin, Huacan,Jiang, Fan,Wang, Tao,Wu, Yun-Dong,Li, Zigang. "An In-tether Chiral Center Modulates the Helicity, Cell Permeability, and Target Binding Affinity of a Peptide". supporting information. p. 8013 - 8017. Retrieved 2016/09/13.
• 2、 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.