Fmoc-δ-azido-Nva-OH

Base Information

• Chemical Name: Fmoc-δ-azido-Nva-OH
• CAS No.: 1097192-04-5
• Molecular Formula: C20H20N4O4
• Molecular Weight: 380.403
• Hs Code.: 2929 90 00
• Mol file: 1097192-04-5.mol

Synonyms:Fmoc-δ-azido-Nva-OH;FMoc-L-azidoornithine;FMoc-d-azido-Nva-OH;FMoc-Orn(N2)-OH;(S)-5-Azido-2-(FMoc-aMino)pentanoic acid;FMOC-L-DELTA-AZIDOORNITHINE;(2S)-N-FMoc-5-azido--Pentenoic acid;5-Azido-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-norvaline

Chemical Property of Fmoc-δ-azido-Nva-OH

Chemical Property:

• PSA: 128.87000
• LogP: 3.72596
• Storage Temp.: 2-8°C

Purity/Quality:

98%Min ^*data from raw suppliers

(S)?-?Fmoc-?2-?amino-?5-?azido-?pentanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)?-?Fmoc-?2-?amino-?5-?azido-?pentanoic Acid is a chiral reagent used in preparing macrocyclic constraints in peptides (peptide stapling) which is an important tool in medicinal peptide chemistry. in addition, (S)?-?Fmoc-?2-?amino-?5-?azido-?pentanoic Acid has been used in the synthesis of clicked peptides.

Technology Process of Fmoc-δ-azido-Nva-OH

There total 9 articles about Fmoc-δ-azido-Nva-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: 92.0%

Fmoc-Orn(Boc)-OH (109425-55-0,118476-89-4) → Nα-(9-fluorenylmethyloxycarbonyl)-azido-L-ornithine (1097192-04-5,1176270-25-9)

Guidance literature:

Fmoc-Orn(Boc)-OH; With water; trifluoroacetic acid; In dichloromethane; for 2h;

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

DOI:10.1002/psc.2968

Reference yield: 85.0%

(S)-5-Amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid (158599-00-9) → Nα-(9-fluorenylmethyloxycarbonyl)-azido-L-ornithine (1097192-04-5,1176270-25-9)

Guidance literature:

(S)-5-Amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid; With copper(ll) sulfate pentahydrate; triflic azide; potassium carbonate; In methanol; water; at 20 ℃; pH=9.5;

With hydrogenchloride; In water; pH=2;

DOI:10.1002/anie.201005846

Reference yield: 71.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + C14H26N4O4 → Nα-(9-fluorenylmethyloxycarbonyl)-azido-L-ornithine (1097192-04-5,1176270-25-9)

Guidance literature:

C₁₄H₂₆N₄O₄; With hydrogenchloride; In ethyl acetate; at 0 - 20 ℃; for 7h;

(fluorenylmethoxy)carbonyl chloride; With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 4.25h;

DOI:10.1016/j.bmcl.2015.06.014

upstream raw materials:

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

2-amino-5-azidopentanoic acid

(S)-5-Amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid

(fluorenylmethoxy)carbonyl chloride

Refernces

• 1、 Holland-Nell, Kai,Meldal, Morten. "Maintaining biological activity by using triazoles as disufide bond mimetics". . p. 5204 - 5206. Retrieved 2011.
• 2、 Pícha, Jan,Budě?ínsky, Milo?,Machá?ková, Kate?ina,Collinsová, Michaela,Jirá?ek, Ji?í. "Optimized syntheses of Fmoc azido amino acids for the preparation of azidopeptides". . p. 202 - 214. Retrieved 2017/04/06.