17301-90-5

Basic information

• Product Name: Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, (5S,5aR,8aR)-
• Synonyms: Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, [5S-(5a,5aa,8ab)]-; Isopodophyllotoxin, 4-deoxy-, (-)- (8CI);(-)-Isodeoxypodophyllotoxin; Isohernandin; NSC 332044
• CAS NO: 17301-90-5
• Molecular Formula: C22H22 O7
• Molecular Weight: 398.4059
• Mol File: 17301-90-5.mol
• Article Data: 44

Chemical Properties

• Boiling Point: 564.5°Cat760mmHg
• Flash Point: 247°C
• Density: 1.304g/cm³
• CAS DataBase Reference: Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, (5S,5aR,8aR)-(CAS DataBase Reference)
• NIST Chemistry Reference: Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, (5S,5aR,8aR)-(17301-90-5)
• EPA Substance Registry System: Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, (5S,5aR,8aR)-(17301-90-5)

Safety Data

• Hazardous Substances Data: 17301-90-5(Hazardous Substances Data)

Upstream product

• 75-11-6 diiodomethane 
• 1173-42-8 6,7-demethylenedeoxypodophyllotoxin 
• 128014-53-9 (+)-γ-apopodophyllic acid 
• 1254-07-5 (5S,6S,7R)-7-Hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 74-95-3 1,1-dibromomethane 
• 160869-33-0 (5R,5aR,8aR)-5-(3,4,5-Trimethoxy-phenyl)-5,5a,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-6,8-dione 
• 518-28-5 podofilox 
• 477-48-5 podophyllotoxone 
• 68415-05-4 α-(3,4,5-trimethoxyphenyl)-α-morpholinoacetonitrile 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 134454-88-9 1-(3',4',5'-trimethoxyphenyl)-1,2-dihydro-4,5-methylenedioxybenzocyclobuten-1-ol 
• 134454-84-5 1-(3,4,5-trimethoxyphenyl)-2-(2'-iodo-4',5'-methylenedioxyphenyl)ethanone 
• 160823-61-0 (5R,6R,7R)-5-(3,4,5-Trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6,7-dicarboxylic acid 
• 160823-58-5 (5R,6S,7R)-5-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6,7-dicarboxylic acid bis-((S)-methoxycarbonyl-phenyl-methyl) ester 

Downstream Products

• 24150-39-8 deoxypicropodophyllin 
• 60073-37-2 2'-bromo-dehydrodesoxypodophyllotoxin 
• 139219-13-9 (5S,6S,7S)-5-(2-Bromo-3,4,5-trimethoxy-phenyl)-7-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 
• 3590-93-0 4'-demethyl-4-deoxypodophyllotoxin 
• 105608-71-7 3',4'-didemethoxy-4-deoxy-3',4'-dihydro-3',4'-dioxopodophyllotoxin 
• 93108-13-5 2′-bromodeoxypodophyllotoxin 
• 477-48-5 podophyllotoxone 
• 518-28-5 podofilox 
• 4375-07-9 epipodophyllotoxin 
• 128443-52-7 5-methoxypodophyllotoxin 
• 119188-52-2 5-methoxypodophyllotoxin-4-O-β-D-glucoside 
• 78215-95-9 desoxypodophyllinic acid ethyl ester 
• 1173-42-8 6,7-demethylenedeoxypodophyllotoxin 
• 3590-88-3 6,7-dihydroxy-9-(3,4,5-trimethoxy-phenyl)-3a,4,9,9a-tetrahydro-3H-naphtho[2,3-c]furan-1-one 

Relevant articles and documents

Chemoenzymatic Total Synthesis of Deoxy-, epi-, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones

Podophyllotoxin is probably the most prominent representative of lignan natural products. Deoxy-, epi-, and podophyllotoxin, which are all precursors to frequently used chemotherapeutic agents, were prepared by a stereodivergent biotransformation and a biocatalytic kinetic resolution of the corresponding dibenzylbutyrolactones with the same 2-oxoglutarate-dependent dioxygenase. The reaction can be conducted on 2 g scale, and the enzyme allows tailoring of the initial, “natural” structure and thus transforms various non-natural derivatives. Depending on the substitution pattern, the enzyme performs an oxidative C?C bond formation by C?H activation or hydroxylation at the benzylic position prone to ring closure.

Synthesis and Computational Studies Demonstrate the Utility of an Intramolecular Styryl Diels-Alder Reaction and Di-t-butylhydroxytoluene Assisted [1,3]-Shift to Construct Anticancer dl-Deoxypodophyllotoxin

Deoxypodophyllotoxin is a secondary metabolite lignan possessing potent anticancer activity with potential as a precursor for known anticancer drugs, but its use is limited by scarcity from natural sources. We here report the total synthesis of racemic de

Synthesis of Cytotoxic Isodeoxypodophyllotoxin Analogs

A series of aryltetralin lignans 7a, 7b, 7c, 7d, 7e, 7f, 7g, 7h, 7i, 7j, 7k, 7l were synthesized as cytotoxic isodeoxypodophyllotoxin analogs. The title compounds 7a, 7b, 7c, 7d, 7e, 7f, 7g, 7h, 7i, 7j, 7k, 7l were synthesized from the reaction of (+)-(R)-4-[benzo(d)(1,3)dioxol-5-ylmethyl]-dihydrofuran-2-(3H)-one with different arylaldehydes to afford benzyl alcohol analogs and subsequent cyclization with trifluoroacetic acid in dichromethane. The preliminary screening of the compounds against viability of blood cancer human cell line K562 revealed that compounds 7d, 7e, and 7f had higher inhibitory activity at 10 μg/mL concentration compared with etoposide as reference drug.