(-)-3-(hydroxymethyl)picropodophyllone

Base Information

• Chemical Name: (-)-3-(hydroxymethyl)picropodophyllone
• CAS No.: 117179-02-9
• Molecular Formula: C₂₃H₂₂O₉
• Molecular Weight: 442.422
• Mol file: 117179-02-9.mol

Synonyms:(-)-3-(hydroxymethyl)picropodophyllone

Chemical Property of (-)-3-(hydroxymethyl)picropodophyllone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-3-(hydroxymethyl)picropodophyllone

There total 19 articles about (-)-3-(hydroxymethyl)picropodophyllone 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: 95.0%

formic acid (64-18-6) + (1R,2R)-2-(tert-butoxylcarbonyl)-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2,3-dihydro-4(1H)-naphthalenone (1428470-94-3) → (-)-3-(hydroxymethyl)picropodophyllone (117179-02-9)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/jo400147f

Reference yield: 80.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 1,2,3,4-tetrahydro-6,7-methylenedioxy-4-oxo-1-(3,4,5-trimethoxyphenyl)naphthalene-2-carboxylic acid (64897-38-7,114381-03-2) → 3-hydroxymethylpicropodophyllon (64897-39-8,117179-02-9)

Guidance literature:

With sodium hydroxide; for 30h; Ambient temperature;

DOI:10.1039/P19820000271

Reference yield:

(-)-(1R,2S)-1-(3,4,5-trimethoxyphenyl)-2-(methoxycarbonyl)-3-<<(tert-butyldimethylsilyl)oxy>methyl>-6,7-(methylenedioxy)-1,2-dihydronaphtalene (117097-47-9) → (-)-3-(hydroxymethyl)picropodophyllone (117179-02-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / N-bromosuccinimide, DMSO / tetrahydrofuran / 6 h / 0 °C

2: 79 percent / azobis(isobutyronitrile), tri-n-butyltin hydride / toluene / 4 h / 120 °C

3: 87 percent / pyridinium dichromate, 3A molecular sieves / CH₂Cl₂ / 4 h / Ambient temperature

4: 1.) 5 N sodium hydroxide, 2.) p-toluenesulfonic acid / 1.) THF, H₂O, 26 h, r. t., 2.) aq. EtOH, 60 - 65 deg C, 24 h

With sodium hydroxide; N-Bromosuccinimide; dipyridinium dichromate; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ja00231a041

upstream raw materials:

formaldehyd

1,2,3,4-tetrahydro-6,7-methylenedioxy-4-oxo-1-(3,4,5-trimethoxyphenyl)naphthalene-2-carboxylic acid

5-Benzo[1,3]dioxol-5-yl-5-hydroxy-2-(3,4,5-trimethoxy-phenyl)-tetrahydro-furan-3-carboxylic acid ethyl ester

(-)-(1R,2S,3S)-1-(3,4,5-trimethoxyphenyl)-2-(methoxycarbonyl)-3-<<(tert-butyldimethylsilyl)oxy>methyl>-6,7-(methylenedioxy)-2,3-dihydro-4(1H)-naphtalenone

Downstream raw materials:

podofilox

picropodophyllotoxin

(+)-4-O-(tert-butyldimethylsilyl)picropodophyllin

(5R,5aR,8aR,9R)-9-((tert-butyldimethylsilyl)oxy)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one

Refernces

• 1、 Andrews, Robert C.,Teague, Simon J.,Meyers, A. I.. "Asymmetric Total Synthesis of (-)-Podophyllotoxin". . p. 7854 - 7858. Retrieved 2007/10/02.