FMoc-Hpg-OH

Base Information

• Chemical Name: FMoc-Hpg-OH
• CAS No.: 942518-21-0
• Molecular Formula: C21H19NO4
• Molecular Weight: 349.386
• Hs Code.: 2924297099
• Mol file: 942518-21-0.mol

Synonyms:FMoc-HoMoGly(Propargyl)-OH;FMoc-Hpg-OH;(2S)-2-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-5-hexynoic acid;Fmoc-L-propargylalanine;Fmoc-L-homopropargylglycine;(2S)-2-(Fmoc-amino)-5-hexynoic acid

Chemical Property of FMoc-Hpg-OH

Chemical Property:

• Boiling Point: 585.7±50.0 °C(Predicted)
• PKA: 3.73±0.10(Predicted)
• PSA: 79.12000
• Density: 1.265±0.06 g/cm3(Predicted)
• LogP: 3.59610

Purity/Quality:

98%Min ^*data from raw suppliers

(2S)-2-(Fmoc-amino)-5-hexynoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of FMoc-Hpg-OH

There total 3 articles about FMoc-Hpg-OH 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: 91.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (S)-2-[bis(tert-butoxycarbonylamino)]-hex-5-ynoic acid tert-butyl ester → 2S-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-hexynoic acid (942518-21-0,1234692-66-0)

Guidance literature:

(S)-2-[bis(tert-butoxycarbonylamino)]-hex-5-ynoic acid tert-butyl ester; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

With hydrogenchloride; Inert atmosphere;

(fluorenylmethoxy)carbonyl chloride; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acs.joc.1c03027

Reference yield:

9-fluorenylmethyl N-succinimidyl carbonate (102774-86-7) + (S)-2-amino-5-hexynoic acid (98891-36-2) → 2S-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-hexynoic acid (942518-21-0,1234692-66-0)

Guidance literature:

(S)-2-amino-5-hexynoic acid; With edetate disodium; sodium carbonate; In water; for 0.166667h; pH=9 - 10;

9-fluorenylmethyl N-succinimidyl carbonate; In water; acetonitrile; at -10 - 20 ℃; for 15h;

DOI:10.1016/j.tetlet.2017.05.007

Reference yield:

4-bromobut-1-yne (38771-21-0) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → 2S-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-hexynoic acid (942518-21-0,1234692-66-0)

Guidance literature:

4-bromobut-1-yne; With Gly-Ni-(S)-2-[N-(N-benzylpropyl)amino]benzophenone; sodium hydroxide; In N,N-dimethyl-formamide; at 20 ℃; for 0.1h; Inert atmosphere;

With hydrogenchloride; In methanol; at 60 ℃; for 0.5h;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; With sodium carbonate; In 1,4-dioxane; at 0 - 20 ℃;

DOI:10.1021/jm201125d

upstream raw materials:

4-bromobut-1-yne

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

9-fluorenylmethyl N-succinimidyl carbonate

(S)-2-amino-5-hexynoic acid

Refernces

• 1、 Li, Bo,Zhang, Jie,Xu, Yongjuan,Yang, Xiaoxiao,Li, Li. "Improved synthesis of unnatural amino acids for peptide stapling". supporting information. p. 2374 - 2377. Retrieved 2017/05/29.