(S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-4-AZIDOBUTANOIC ACID

Base Information

• Chemical Name: (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-4-AZIDOBUTANOIC ACID
• CAS No.: 942518-20-9
• Molecular Formula: C19H18N4O4
• Molecular Weight: 366.376
• Hs Code.: 2929 90 00
• Mol file: 942518-20-9.mol

Synonyms:(2S)-N-FMoc-4-azido-butanoic acid;

Chemical Property of (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-4-AZIDOBUTANOIC ACID

Chemical Property:

• Melting Point: 124.0 to 128.0 °C
• PSA: 125.38000
• LogP: 3.52236
• Storage Temp.: ?20°C

Purity/Quality:

99%min ^*data from raw suppliers

Fmoc-L-Aha-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-4-AZIDOBUTANOIC ACID

There total 5 articles about (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-4-AZIDOBUTANOIC ACID 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: 92.0%

Nα-(9-fluorenylmethoxycarbonyl)-L-2,4-diaminobutyric acid (161420-87-7,201484-12-0) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-azidobutanoic acid (942518-20-9)

Guidance literature:

With copper(ll) sulfate pentahydrate; triflic azide; sodium hydrogencarbonate; In methanol; dichloromethane; water; at 20 ℃;

DOI:10.1002/psc.2968

Reference yield:

N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine (71989-20-3) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-azidobutanoic acid (942518-20-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: [bis-(trifluoroacetoxy)iodo]benzene / water; N,N-dimethyl-formamide / 0.25 h

1.2: 14 h / 20 °C

2.1: imidazole-1-sulfonyl azide hydrochloride; potassium carbonate; copper(II) sulfate / methanol; dichloromethane; water / 18 h / pH 9

With imidazole-1-sulfonyl azide hydrochloride; [bis-(trifluoroacetoxy)iodo]benzene; potassium carbonate; copper(II) sulfate; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1055/s-0030-1260950

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (2S)-2-amino-4-azidobutanoic acid (120042-14-0) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-azidobutanoic acid (942518-20-9)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 3h; pH=8;

DOI:10.1002/ejoc.200800717

upstream raw materials:

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

(2S)-2-amino-4-azidobutanoic acid

N_α-(9-fluorenylmethoxycarbonyl)-L-2,4-diaminobutyric acid

N₂-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine

Refernces

• 1、 Li, Jian,Guan, Dongliang,Chen, Feifei,Shi, Weiwei,Lan, Lefu,Huang, Wei. "Total and Semisyntheses of Polymyxin Analogues with 2-Thr or 10-Thr Modifications to Decipher the Structure-Activity Relationship and Improve the Antibacterial Activity". . p. 5746 - 5765. Retrieved 2021/06/01.
• 2、 Wiedmann, Mareike M.,Tan, Yaw Sing,Wu, Yuteng,Aibara, Shintaro,Xu, Wenshu,Sore, Hannah F.,Verma, Chandra S.,Itzhaki, Laura,Stewart, Murray,Brenton, James D.,Spring, David R.. "Development of Cell-Permeable, Non-Helical Constrained Peptides to Target a Key Protein–Protein Interaction in Ovarian Cancer". supporting information. p. 524 - 529. Retrieved 2017/01/07.