(2S,6S)-4-Methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-one

Base Information

• Chemical Name: (2S,6S)-4-Methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-one
• CAS No.: 24316-19-6
• Molecular Formula: C18H21NO4
• Molecular Weight: 315.369
• DSSTox Substance ID: DTXSID3048231
• Nikkaji Number: J132.872G
• Wikidata: Q105289075
• Mol file: 24316-19-6.mol

Synonyms:(2S,6S)-4-Methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-one;Cephalotaxine, 3-deoxy-3-oxo-;3-Deoxy-3-oxocephalotaxine;SCHEMBL3761328;DTXSID3048231;38750-57-1

Chemical Property of (2S,6S)-4-Methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-one

Chemical Property:

• Appearance/Colour: White powder with faint yellow cast
• Vapor Pressure: 1.27E-10mmHg at 25°C
• Melting Point: 131-132 °C(Solv: benzene (71-43-2))
• Refractive Index: 1.664
• Boiling Point: 495.2 °C at 760 mmHg
• PKA: 13.30±0.40(Predicted)
• Flash Point: 253.3 °C
• PSA: 51.16000
• Density: 1.38 g/cm³
• LogP: 1.73230
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 313.13140809
• Heavy Atom Count: 23
• Complexity: 561

Purity/Quality:

97% ^*data from raw suppliers

Cephalotaxine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC23CCCN2CCC4=CC5=C(C=C4C3C1=O)OCO5
• Isomeric SMILES: COC1=C[C@]23CCCN2CCC4=CC5=C(C=C4[C@@H]3C1=O)OCO5
• General Description: Cephalotaxine is a pentacyclic alkaloid known for its antileukemic properties, characterized by a complex structure that has been synthesized through a catalytic asymmetric approach involving a tandem hydroamination/semipinacol rearrangement reaction. This method highlights its efficient enantioselective synthesis and potential relevance in medicinal chemistry.

Technology Process of (2S,6S)-4-Methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-one

There total 9 articles about (2S,6S)-4-Methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-one 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: 50.0%

(±)-cephalotaxinone (38750-57-1,38848-26-9) → cephalotaxine (24316-19-6) + (-)-Cephalotaxinone (38750-57-1)

Guidance literature:

With Noyori's catalyst; formic acid; triethylamine; at 40 ℃; for 48h; Sealed tube; Inert atmosphere;

Reference yield: 26.0%

→ lithium (7439-93-2) + cephalotaxine (24316-19-6)

Guidance literature:

Reference yield:

methyl magnesium iodide (917-64-6) + Methyl 3-carbocephalotaxyl-3-hydroxy-7-oxooctanoate (84395-19-7) → homoharringtonine (26833-87-4) + cephalotaxine (24316-19-6)

Guidance literature:

In tetrahydrofuran; 1) -78 degC, 2) -20 degC, 30 min;

DOI:10.1021/jo00174a031

upstream raw materials:

methyl magnesium iodide

Methyl 3-carbocephalotaxyl-3-hydroxy-7-oxooctanoate

(±)-cephalotaxinone

Downstream raw materials:

(3aR)-1t-benzoyloxy-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]azepine

(3aR)-1t-benzyloxycarbonyloxy-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]azepine

(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

3t-phenyl-acrylic 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

Refernces

Formal synthesis of (-)-cephalotaxine based on a tandem hydroamination/semipinacol rearrangement reaction

10.1002/asia.201101029

The research focuses on the formal synthesis of (-)-Cephalotaxine, an alkaloid with unique pentacyclic structure and antileukemic activity. The study proposes a highly efficient catalytic asymmetric formal synthesis using a tandem hydroamination/semipinacol rearrangement reaction. Key reactants include 1-azaspirocyclic building block 4, alkyne 8, and chiral phosphoric acid 5 as a catalyst. The research involves the synthesis of various substrates 8 with different protecting groups, optimization of reaction conditions, and the examination of the reaction's efficiency and enantioselectivity. Analyses used include chiral-HPLC for determining yields and enantiomeric excess (ee), as well as X-ray crystallography for absolute configuration determination. The study also discovered an enantiomer separation phenomenon on silica gel during purification, which could have implications for the synthesis of other complex compounds.