16-Methoxytabersonine

Base Information

• Chemical Name: 16-Methoxytabersonine
• CAS No.: 27773-39-3
• Molecular Formula: C₂₂H₂₆N₂O₃
• Molecular Weight: 366.46
• UNII: VX294XSR6T
• DSSTox Substance ID: DTXSID301032205
• Nikkaji Number: J450.691J
• Wikipedia: 16-Methoxytabersonine
• Wikidata: Q21099580
• Metabolomics Workbench ID: 52821
• ChEMBL ID: CHEMBL1165751
• Mol file: 27773-39-3.mol

Synonyms:11-methoxytabersonine

Chemical Property of 16-Methoxytabersonine

Chemical Property:

• PSA: 50.80000
• LogP: 3.30570
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 366.19434270
• Heavy Atom Count: 27
• Complexity: 716

Purity/Quality:

99% ^*data from raw suppliers

Ervamycine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC12CC(=C3C4(C1N(CC4)CC=C2)C5=C(N3)C=C(C=C5)OC)C(=O)OC
• Isomeric SMILES: CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)CC=C2)C5=C(N3)C=C(C=C5)OC)C(=O)OC
• Description: This alkaloid from Vinca herbacea has been isolated as the crystalline hydrochloride, m.p. 184-6°C (dec.). The free base has [α]23D - 310° ± 2° (c 0.32, CHC13). Hydrogenation over Pt02 gives the 6:7-dihydro derivative which has [α]26D - 412.8° (c 0.606, CHCI3). When heated at 100°C with 5N-HC1, the latter is simultaneously hydrolyzed and decarboxylated to furnish 16-methoxy- 1: 2-dehydro-( - )-aspidospermidine.

Technology Process of 16-Methoxytabersonine

There total 4 articles about 16-Methoxytabersonine 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:

3',4'-anhydrovinblastine → hoerhammericine (19459-04-2,61825-77-2,109063-93-6,109063-94-7) + hoerhammerinine (19459-05-3) + 19-epivindolinine (27773-39-3,86116-70-3,106356-44-9) + ajmalicine (483-04-5)

Guidance literature:

at 27 ℃; Yield given. Further byproducts given. Yields of byproduct given; C_. roseus, 200GW cell line;

DOI:10.1016/S0040-4020(01)88620-8

Reference yield:

3',4'-anhydrovinblastine → hoerhammericine (19459-04-2,61825-77-2,109063-93-6,109063-94-7) + 19-epivindolinine (27773-39-3,86116-70-3,106356-44-9) + catharanthine (1212401-29-0) + ajmalicine (483-04-5)

Guidance literature:

at 27 ℃; Yield given. Further byproducts given. Yields of byproduct given; C_. roseus 200GW cell line;

DOI:10.1016/S0040-4020(01)88620-8

Reference yield:

3',4'-anhydrovinblastine → hoerhammericine (19459-04-2,61825-77-2,109063-93-6,109063-94-7) + 19-epivindolinine (27773-39-3,86116-70-3,106356-44-9) + 16-methoxytabersonine (27773-39-3,86116-70-3,106356-44-9) + ajmalicine (483-04-5)

Guidance literature:

at 27 ℃; Yield given. Further byproducts given. Yields of byproduct given; C_. roseus, 200GW cell line;

DOI:10.1016/S0040-4020(01)88620-8

Downstream raw materials:

(3aR,3a¹R,4R,5S,5aR,10bR)-methyl 3a-ethyl-4,5-dihydroxy-8-methoxy-6-methyl-3a,3a¹,4,5,5a,6,11,12-octahydro-1H-indolizino-[8,1-cd]carbazole-5-carboxylate

vindoline

(-)-deacetylvindoline

(-)-vindoline

Refernces