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 
• 518-28-5 podofilox 
• 29943-42-8 Tetrahydro-4H-pyran-4-one 
• 477-48-5 podophyllotoxone 
• 1072-72-6 Tetrahydrothiopyran-4-one 
• 563-80-4 3-methyl-butan-2-one 
• 119-61-9 benzophenone 
• 6258-32-8 (dl)-5-(3,4,5-trimethoxyphenyl)-8a,9-dihydrofuro[3′,4’:6,7]-naphtho[2,3-d][1,3]dioxol-6(8H)-one 
• 1254-07-5 7-Hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 17187-77-8 (R)-(+)-3-piperonyl-4-butanolide 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 17301-91-6 (3R*,4R*)-3-(3,4,5-trimethoxybenzyl)-4-(3,4-methylenedioxybenzyl)-4,5-dihydro-2(3H)-furanone 
• 76886-74-3 C₂₄H₂₂O₁₀ 

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 
• 128443-52-7 5-methoxypodophyllotoxin 
• 119188-52-2 5-methoxypodophyllotoxin-4-O-β-D-glucoside 
• 518-29-6 β-peltatin 
• 1445712-18-4 C₃₃H₂₅N₃O₆ 
• 1445712-19-5 C₃₃H₂₄IN₃O₆ 
• 1445712-20-8 C₃₄H₂₇N₃O₇ 
• 1445712-21-9 C₃₄H₂₇N₃O₇ 
• 1445712-22-0 C₃₅H₂₉N₃O₈ 
• 1445712-28-6 C₃₃H₂₅N₃O₆ 
• 1445712-31-1 C₃₄H₂₇N₃O₇ 
• 1445712-32-2 C₃₄H₂₇N₃O₇ 

Relevant articles and documents

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.

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.