(+)-Isofebrifugine

Base Information

• Chemical Name: (+)-Isofebrifugine
• CAS No.: 24159-07-7
• Molecular Formula: C₁₆H₁₉N₃O₃
• Molecular Weight: 301.345
• Hs Code.: 2933990090
• European Community (EC) Number: 683-166-2
• Nikkaji Number: J1.445.080G
• Wikipedia: Febrifugine
• Wikidata: Q104250952
• Metabolomics Workbench ID: 131459
• ChEMBL ID: CHEMBL3348937
• Mol file: 24159-07-7.mol

Synonyms:febrifugine;isofebrifugine

Chemical Property of (+)-Isofebrifugine

Chemical Property:

• Vapor Pressure: 3.76E-11mmHg at 25°C
• Melting Point: 139-140°; mp 154-156°
• Boiling Point: 508.2 °C at 760 mmHg
• PKA: 14.61±0.40(Predicted)
• Flash Point: 261.1 °C
• PSA: 84.22000
• Density: 1.39 g/cm³
• LogP: 0.79740
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 301.14264148
• Heavy Atom Count: 22
• Complexity: 466

Purity/Quality:

≥98% ^*data from raw suppliers

Febrifugine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(NC1)CC(=O)CN2C=NC3=CC=CC=C3C2=O)O
• Isomeric SMILES: C1C[C@@H]([C@@H](NC1)CC(=O)CN2C=NC3=CC=CC=C3C2=O)O
• General Description: Febrifugine is an antimalarial compound that can be synthesized through complementary chemoenzymatic routes to produce both its (+)- and (-)-enantiomers. These synthetic strategies involve key intermediates such as cyanohydrin or allysine ethylene acetal, along with protective groups (Boc, MOM), reducing agents (LiAlH4), and oxidative reagents (mCPBA, OsO4/NaIO4) to construct the quinazolone-containing side chain and the febrifugine skeleton. The methods highlight the utility of chemoenzymatic approaches in accessing complex natural products and their derivatives for potential therapeutic applications.

Technology Process of (+)-Isofebrifugine

There total 126 articles about (+)-Isofebrifugine 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: 97.0%

(-)-(2R,3S)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate → febrifugine (24159-07-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 1.5h;

DOI:10.1016/j.tet.2017.07.041

Reference yield: 93.0%

(2R,3S)-3-Benzyloxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester (304665-11-0) → febrifugine (24159-07-7)

Guidance literature:

With hydrogenchloride; In water; Heating;

DOI:10.1021/ol006384f

Reference yield: 92.0%

(2R,3S)-3-benzyloxy-2-[2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester (304665-12-1) → febrifugine (24159-07-7)

Guidance literature:

With hydrogenchloride; for 26h; Heating;

DOI:10.3987/COM-05-S(T)12

upstream raw materials:

3-{3-[(2RS,3SR)-1-ethoxycarbonyl-3-methoxy-2-piperidinyl]-2-oxopropyl}-4(3H)-quinazolinone

(E)-benzyl (4-hydroxy-7-oxooct-5-en-1-yl)carbamate

1-(benzyloxycarbonyl)-1,2,3,4-tetrahydropyridine

benzyl 2,3-dihydroxy-1-piperidinecarboxylate

Refernces

Complementary chemoenzymatic routes to both enantiomers of febrifugine

10.1039/b901670h

The research details two complementary chemoenzymatic strategies for the synthesis of both enantiomers of febrifugine, an antimalarial compound. The first approach starts from cyanohydrin, which undergoes reductive cyclization and subsequent reactions to introduce the quinazolone-containing side chain, leading to (+)-febrifugine. Key chemicals involved include cyanohydrin, allylsilane, LiAlH4 for reduction, Boc and MOM groups for protection, mCPBA for epoxidation, and isatoic anhydride for the introduction of the anthranilic acid moiety. The second strategy begins with allysine ethylene acetal, which is converted into the corresponding N,O-acetal and then reacts with 2-(chloromethyl)allylsilane and quinazolone to form the febrifugine skeleton, eventually yielding ent-febrifugine after several transformations. This route involves allysine ethylene acetal, BF3·OEt2 for activation, quinazolone as a nucleophile, and osmium tetroxide and sodium periodate for oxidative cleavage. Both strategies demonstrate the versatility of chemoenzymatic methods in constructing complex natural products and provide pathways for the synthesis of febrifugine analogues.

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