477-48-5

Basic information

• Product Name: (5R)-5,8,8aβ,9-Tetrahydro-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6(5aβH),9-dione
• Synonyms: (-)-Picropodophyllone;Picropodophyllone;Picropodophyllotoxone;Picropodophyllon
• CAS NO: 477-48-5
• Molecular Formula: C₂₂H₂₀O₈
• Molecular Weight: 412.3894
• Mol File: 477-48-5.mol
• Article Data: 41

Chemical Properties

• Boiling Point: 602.3°Cat760mmHg
• Flash Point: 263.5°C
• Appearance: /
• Density: 1.365g/cm³
• CAS DataBase Reference: (5R)-5,8,8aβ,9-Tetrahydro-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6(5aβH),9-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (5R)-5,8,8aβ,9-Tetrahydro-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6(5aβH),9-dione(477-48-5)
• EPA Substance Registry System: (5R)-5,8,8aβ,9-Tetrahydro-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6(5aβH),9-dione(477-48-5)

Safety Data

• Hazardous Substances Data: 477-48-5(Hazardous Substances Data)

Usage

General Description

"(5R)-5,8,8aβ,9-Tetrahydro-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6(5aβH),9-dione" is a complex chemical compound with a fused ring system. It contains a furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6(5aβH),9-dione core structure and a 3,4,5-trimethoxyphenyl substituent. (5R)-5,8,8aβ,9-Tetrahydro-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6(5aβH),9-dione's systematic name indicates the stereochemistry at the C-5 position, with the (5R) configuration. The presence of multiple functional groups, including furan, naphthoquinone, and trimethoxyphenyl, makes this compound intriguing for potential pharmaceutical or medicinal applications. However, due to its complex structure, extensive research would be needed to fully understand its properties and potential uses.

Upstream product

• 1180-34-3 podophyllotoxinyl acetate 
• 477-48-5 podophyllotoxone 
• 16481-54-2 podophyllotoxin-7′-O-β-D-glucopyranoside 
• 477-51-0 deoxypodophyllotoxin 
• 518-28-5 podofilox 
• 117179-02-9 (-)-3-(hydroxymethyl)picropodophyllone 
• 477-47-4 picropodophyllotoxin 
• 101707-95-3 Benzo[1,3]dioxol-5-yl-(tert-butyl-dimethyl-silanyloxy)-acetonitrile 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 56579-86-3 2-(3,4-methylenedioxyphenyl)-1,3-dithiane 
• 90359-54-9 3,4-methylenedioxycinnamyl 3-(3,4,5-trimethoxyphenyl)acrylate 
• 620116-56-5 (5S,5aS,8aR,9R)-5-(Dimethyl-phenyl-silanyl)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester 
• 620116-55-4 (5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-(3,4,5-trimethoxy-phenoxythiocarbonyloxymethyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester 
• 620116-47-4 9-(tert-butyl-dimethyl-silanyloxy)-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 

Downstream Products

• 130322-37-1 C₂₂H₂₂O₈ 
• 120090-82-6 thuriferic acid 
• 120090-94-0 (5R,6S,7S)-7-Methoxymethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 477-47-4 picropodophyllotoxin 
• 55515-07-6 (1α,2α,3α)-podophyllotoxin 
• 157904-78-4 <5R-(5α,6α)>-5,6,7,8-tetrahydro-7-methylidene-8-oxo-5-(3,4,5-trimethoxyphenyl)naphtho<2,3-d><1,3>dioxole-6-carboxylic acid 
• 4375-07-9 epipodophyllotoxin 
• 518-28-5 podofilox 
• 191283-12-2 (Z)-podophyllotoxone O-methyloxime 
• 138935-77-0 4-Hydroxy-3-methyl-6,7-(methylenedioxy)-1-(3,4,5-trimethoxyphenyl)-2-naphthoic acid 
• 112711-16-7 (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 
• 108448-52-8 (+)-4-O-(tert-butyldimethylsilyl)picropodophyllin 
• 121677-84-7 (3aR)-2-phenyl-5c-(3,4,5-trimethoxy-phenyl)-(3ar)-3,3a,4,5-tetrahydro-2H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]indazole-4c-carboxylic acid methyl ester 
• 122215-70-7 (3aR)-2-(4-bromo-phenyl)-5c-(3,4,5-trimethoxy-phenyl)-(3ar)-3,3a,4,5-tetrahydro-2H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]indazole-4c-carboxylic acid methyl ester 

Relevant articles and documents

Synthesis and In Vitro Anticancer Activity of Triazolyl Analogs of Podophyllotoxin, a Naturally Occurring Lignin

Abstract: A series of triazolyl-modified podophyllotoxin analogs have been designed and synthesized by utilizing Huisgen 1,3-dipolar cycloaddition in order to develop potent antitumor agents. The synthesized analogs were assessed for in vitro anticancer a

Scalable Aerobic Oxidation of Alcohols Using Catalytic DDQ/HNO3

A selective, practical, and scalable aerobic oxidation of alcohols is described that uses catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and HNO3, with molecular oxygen serving as the terminal oxidant. The method was successfully applied to the oxidation of a wide range of benzylic, propargylic, and allylic alcohols, including two natural products, namely, carveol and podophyllotoxin. The conditions are also applicable to the selective oxidative deprotection of p-methoxybenzyl ethers.

Asymmetric Chemoenzymatic Synthesis of (?)-Podophyllotoxin and Related Aryltetralin Lignans

(?)-Podophyllotoxin is one of the most potent microtubule depolymerizing agents and has served as an important lead compound in antineoplastic drug discovery. Reported here is a short chemoenzymatic total synthesis of (?)-podophyllotoxin and related aryltetralin lignans. Vital to this approach is the use of an enzymatic oxidative C?C coupling reaction to construct the tetracyclic core of the natural product in a diastereoselective fashion. This strategy allows gram-scale access to (?)-deoxypodophyllotoxin and is readily adaptable to the preparation of related aryltetralin lignans.