Alkaloid C from cephalotaxus

Base Information

• Chemical Name: Alkaloid C from cephalotaxus
• CAS No.: 26833-85-2
• Molecular Formula: C₂₈H₃₇NO₉
• Molecular Weight: 531.603
• European Community (EC) Number: 636-661-2
• Wikidata: Q105025092
• ChEMBL ID: CHEMBL175608
• Mol file: 26833-85-2.mol

Synonyms:2'R-harringtonine;cephalotaxine, 4-methyl (2R)-2-hydroxy-2-(3-hydroxy-3-methylbutyl)butanedioate (ester);harringtonin;harringtonine;harringtonine hydrochloride;harringtonine, (R)-isomer;harringtonine, (S)-isomer;harringtonine, racemic mixture

Chemical Property of Alkaloid C from cephalotaxus

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 2.17E-19mmHg at 25°C
• Melting Point: 73-75 °C
• Refractive Index: 1.609
• Boiling Point: 679.419 °C at 760 mmHg
• PKA: 11.62±0.29(Predicted)
• Flash Point: 364.7 °C
• PSA: 123.99000
• Density: 1.35 g/cm³
• LogP: 2.12850
• Storage Temp.: 2-8°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 531.24683176
• Heavy Atom Count: 38
• Complexity: 953

Purity/Quality:

99% ^*data from raw suppliers

Harringtonine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(CCC(CC(=O)OC)(C(=O)OC1C2C3=CC4=C(C=C3CCN5C2(CCC5)C=C1OC)OCO4)O)O
• Description: The full structure of harringtonine has now been established from a study of the hydrolysis products of this base. Harringtonine is a natural alkaloid that inhibits protein synthesis at low micromolar concentrations. It immobilizes ribosomes immediately after the initiation of translation. While harringtonine has drawn some interest in mitigating cancer, its homolog homoharrington is more effective, particularly for chronic myelogenous leukemia. The ability of harringtonine to immobilize initiating ribosomes can be used to capture ribosome-protected mRNA fragments for evaluating translation.
• Uses: specific anti-leukemia drug A natural product with significant antitumor activities.

Technology Process of Alkaloid C from cephalotaxus

There total 14 articles about Alkaloid C from cephalotaxus 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%

C34H51NO9Si → harringtonine (26833-85-2)

Guidance literature:

With triethylamine tris(hydrogen fluoride); triethylamine; In acetonitrile; at 80 ℃; for 72h;

DOI:10.1021/acs.orglett.7b00743

Reference yield:

C35H42BrNO9 → harringtonine (26833-85-2)

Guidance literature:

With palladium on activated charcoal; hydrogen; sodium acetate; In methanol; at 20 ℃; for 24h; under 760.051 Torr;

Reference yield:

4-benzyloxy-7,7-dimethyl-2-oxo-oxepane-4-carbonyl chloride (68423-50-7) → harringtonine (26833-85-2)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine

2: methanol

3: H₂ / Pd-C / acetic acid

With hydrogen; palladium on activated charcoal; In pyridine; methanol; acetic acid;

DOI:10.1021/jo01315a015

upstream raw materials:

(Ξ)-2-benzyloxy-2-(3-hydroxy-3-methyl-butyl)-succinic acid 1-((3aR)-2-methoxy-(3arC⁴,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl) ester 4-methyl ester

4-benzyloxy-7,7-dimethyl-2-oxo-oxepane-4-carbonyl chloride

(Ξ)-4-benzyloxy-7,7-dimethyl-2-oxo-oxepane-4-carboxylic acid (3aR)-2-methoxy-(3arC⁴,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl ester

cephalotaxine

Refernces

• 1、 Ma, Guo-Zhen,Li, Peng-Fei,Liu, Lu,Li, Wei-Dong Z.,Chen, Li. "Diastereoselective Synthesis of Cephalotaxus Esters via Asymmetric Mukaiyama Aldol Reaction". . p. 2250 - 2253. Retrieved 2017/05/12.