Methylneoquassin

Base Information

• Chemical Name: Methylneoquassin
• CAS No.: 89498-93-1
• Molecular Formula: C₂₃H₃₂O₆
• Molecular Weight: 404.503
• Mol file: 89498-93-1.mol

Synonyms:2,12,16β-trimethoxypicrasa-2,12-diene-1,11-dione

Chemical Property of Methylneoquassin

Chemical Property:

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Methylneoquassin ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methylneoquassin

There total 11 articles about Methylneoquassin 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:

1α-benzyloxy-12α,13α-epoxypicras-14-ene-2,16-dione (204130-81-4) → 2,12,16β-trimethoxypicrasa-2,12-diene-1,11-dione (89498-93-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 92 percent / H₂ / Pd/C / ethanol / 48 h / 20 °C

2.1: DIBAL-H / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.1: conc. HCl / 1 h / 0 °C

4.1: DMSO; TFAA; Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: 7 mg / NaH / dimethylformamide / 1 h / -20 °C

6.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

6.2: MoOPH / tetrahydrofuran / -78 - 0 °C

7.1: DMSO; TFAA; Et₃N / CH₂Cl₂ / -78 - 20 °C

8.1: 5.7 mg / NaH / dimethylformamide / 0.67 h / -20 °C

With hydrogenchloride; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Catalytic hydrogenation / 2.1: Reduction / 3.1: Methylation / 4.1: Swern oxidation / 5.1: Methylation / 6.1: Deprotonation / 6.2: Hydroxylation / 7.1: Swern oxidation / 8.1: Methylation;

DOI:10.1021/jo000877g

Reference yield:

(3aS,5S,6aR,7aS,8S,11aS,11bS,11cS)-5,10-Dimethoxy-3,8,11a,11c-tetramethyl-3a,4,5,6a,7,7a,8,11a,11b,11c-decahydro-3H-6-oxa-benzo[de]anthracene-1,2,11-trione + methyl iodide (74-88-4) → 2,12,16β-trimethoxypicrasa-2,12-diene-1,11-dione (89498-93-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at -20 ℃;

DOI:10.1021/jo9718962

Reference yield:

(3aR,5S,6aR,7aS,8S,11aS,11bS,11cS)-2-Hydroxy-5,10-dimethoxy-3,8,11a,11c-tetramethyl-3a,4,5,6a,7,7a,8,11a,11b,11c-decahydro-6-oxa-benzo[de]anthracene-1,11-dione + methyl iodide (74-88-4) → 2,12,16β-trimethoxypicrasa-2,12-diene-1,11-dione (89498-93-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at -20 ℃; for 0.666667h;

DOI:10.1021/jo000877g

upstream raw materials:

methanol

picrasinoside-B

methyl iodide

1α,12α-dihydroxypicrasane-2,16-dione

Downstream raw materials:

quassin

Refernces

• 1、 Shing, Tony K. M.,Jiang, Qin,Mak, Thomas C. W.. "Total Synthesis of (+)-Quassin from (+)-Carvone". . p. 2056 - 2057. Retrieved 2007/10/03.
• 2、 Okano, Masayoshi,Fujita, Tomoyuki,Fukamiya, Narihiko,Aratani, Takaaki. "NEW QUASSINOID GLYCOSIDES AND HEMIACETALS FROM PICRASMA AILANTHOIDES PLANCHON. PICRASINOIDE-B,-C,-D,-E,-F, AND -G, AND PICRASINOL-A AND -B". . p. 221 - 224. Retrieved 2007/10/02.