Aplyronine C

Base Information

• Chemical Name: Aplyronine C
• CAS No.: 151923-86-3
• Molecular Formula: C₅₃H₉₀N₂O₁₂
• Molecular Weight: 947.304
• DSSTox Substance ID: DTXSID30420070
• Metabolomics Workbench ID: 143795
• ChEMBL ID: CHEMBL264271
• Mol file: 151923-86-3.mol

Synonyms:aplyronine C

Chemical Property of Aplyronine C

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 944.4°C at 760 mmHg
• Flash Point: 525°C
• Density: 1.09g/cm³
• XLogP3: 8.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 19
• Exact Mass: 946.64937631
• Heavy Atom Count: 67
• Complexity: 1610

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(=CCC(CC(C=CCC(OC(=O)C=CC=CCC(C(C1O)C)O)C(C)C(C(C)CCC(C(C)C(C(C)C=CN(C)C=O)OC(=O)C)OC(=O)C(C)N(C)C)O)OC)C)C)OC
• Isomeric SMILES: C[C@@H]1CC[C@@H](/C(=C/C[C@H](C[C@H](/C=C/C[C@H](OC(=O)/C=C/C=C/C[C@H]([C@H]([C@@H]1O)C)O)[C@@H](C)[C@H]([C@@H](C)CC[C@H]([C@H](C)[C@@H]([C@H](C)/C=C/N(C)C=O)OC(=O)C)OC(=O)C(C)N(C)C)O)OC)C)/C)OC

Technology Process of Aplyronine C

There total 12 articles about Aplyronine C 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: 89.0%

C71H132N2O12Si3 (1440972-85-9) → aplyronine C (151923-86-3)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; at 0 - 20 ℃;

DOI:10.1021/ol401327r

Reference yield:

N,N-dimethyl-L-alanine (2812-31-9) + C66H123NO11Si3 → aplyronine C (151923-86-3)

Guidance literature:

Multi-step reaction with 2 steps

1: camphor-10-sulfonic acid; dmap; dicyclohexyl-carbodiimide / 11 h / 20 °C

2: pyridine hydrogenfluoride / tetrahydrofuran; pyridine / 0 - 20 °C

With dmap; camphor-10-sulfonic acid; pyridine hydrogenfluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; pyridine;

DOI:10.1021/ol401327r

Reference yield:

C66H121NO12Si3 → aplyronine C (151923-86-3)

Guidance literature:

Multi-step reaction with 5 steps

1: Burgess Reagent / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

2: triphenylphosphine; copper(II) acetate monohydrate; 1,1,3,3-Tetramethyldisiloxane / toluene / 5 h / 20 °C / Inert atmosphere

3: zinc(II) tetrahydroborate / diethyl ether / 11 h / 0 °C

4: 4-(dimethylamino)pyridine hydrochloride; dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere

5: pyridine hydrogenfluoride; pyridine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; zinc(II) tetrahydroborate; Burgess Reagent; 1,1,3,3-Tetramethyldisiloxane; 4-(dimethylamino)pyridine hydrochloride; copper(II) acetate monohydrate; pyridine hydrogenfluoride; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1039/c7ob03204h

upstream raw materials:

N,N-dimethyl-L-alanine

C₇₁H₁₃₂N₂O₁₂Si₃

C₆₆H₁₁₉NO₁₁Si₃

C₆₆H₁₂₁NO₁₁Si₃

Refernces

• 1、 Paterson, Ian,Fink, Sarah J.,Lee, Lydia Y. W.,Atkinson, Stephen J.,Blakey, Simon B.. "Total synthesis of aplyronine C". . p. 3118 - 3121. Retrieved 2013/07/26.