3',4'-Anhydrovinblastine

Base Information

• Chemical Name: 3',4'-Anhydrovinblastine
• CAS No.: 38390-45-3
• Deprecated CAS: 1076210-07-5,119264-84-5,120478-94-6,1263285-71-7,1620695-06-8
• Molecular Formula: C₄₆H₅₆N₄O₈
• Molecular Weight: 792.973
• UNII: 5B622U08B3
• DSSTox Substance ID: DTXSID70873203
• Wikidata: Q27261776
• NCI Thesaurus Code: C2526
• Mol file: 38390-45-3.mol

Synonyms:3',4'-anhydrovinblastine;3',4'-anhydrovinblastine, (18'alpha)-isomer

Chemical Property of 3',4'-Anhydrovinblastine

Chemical Property:

• Appearance/Colour: white crystal power
• Melting Point: 205-207oC
• PKA: 11.36±0.60(Predicted)
• PSA: 133.87000
• Density: 1.35 g/cm³
• LogP: 4.73690
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 792.40981476
• Heavy Atom Count: 58
• Complexity: 1710

Purity/Quality:

99% ^*data from raw suppliers

Anhydrovinblastine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=CC2CC(C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC
• Isomeric SMILES: CCC1=C[C@H]2C[C@@](C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)[C@]78CCN9[C@H]7[C@@](C=CC9)([C@H]([C@@]([C@@H]8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC
• Recent ClinicalTrials: Anhydrovinblastine in Treating Patients With Advanced Recurrent Solid Tumors

Technology Process of 3',4'-Anhydrovinblastine

There total 16 articles about 3',4'-Anhydrovinblastine 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: 90.0%

catharanthine + vindoline (2182-14-1) → anhydrovinblastine (38390-45-3,56083-20-6,61246-76-2,105815-31-4)

Guidance literature:

catharanthine; vindoline; With hydrogenchloride; 2,2,2-trifluoroethanol; iron(III) chloride hexahydrate; In water; at 25 ℃; for 2h; Inert atmosphere;

With sodium tetrahydroborate; In water; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/ml200236a

Reference yield: 90.0%

catharinthine (2468-21-5) + vindoline (2182-14-1) → anhydrovinblastine (38390-45-3,56083-20-6,61246-76-2,105815-31-4)

Guidance literature:

catharinthine; vindoline; With iron(III) chloride hexahydrate; at 25 ℃;

With sodium tetrahydroborate; at 0 ℃;

DOI:10.1016/j.bmcl.2010.09.091

Reference yield: 85.0%

Catharanthine + vindoline (2182-14-1) → anhydrovinblastine (38390-45-3,56083-20-6,61246-76-2,105815-31-4)

Guidance literature:

Catharanthine; vindoline; With hydrogenchloride; iron(III) chloride; at 35 ℃; aqueous glycine buffer;

With ammonium hydroxide; sodium tetrahydroborate; In water;

DOI:10.1021/jm801064y

upstream raw materials:

Catharanthine hydrogensulfate

vindoline

catharinthine

anhydrovinblastine eniminium

Downstream raw materials:

Vincristine

vinblastin

vinleurosine

catharine

Refernces

• 1、 Boon, Byron A.,Boger, Dale L.. "Triarylaminium Radical Cation Promoted Coupling of Catharanthine with Vindoline: Diastereospecific Synthesis of Anhydrovinblastine and Reaction Scope". supporting information. p. 14349 - 14355. Retrieved 2019/10/11.
• 2、 Ngo, Quoc Anh,Nguyen, Le Anh,Vo, Ngoc Binh,Nguyen, Thuy Hang,Roussi, Fanny,Nguyen, The Hung,Nguyen, Van Tuyen. "Synthesis and antiproliferativeactivity of new vinca alkaloids containing an α,β-unsaturated aromatic side chain". . p. 5597 - 5600. Retrieved 2015/11/17.