60325-08-8

Basic information

• Product Name: (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione
• Synonyms: (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione;Nanaomycin D
• CAS NO: 60325-08-8
• Molecular Formula: C₁₆H₁₂O₆
• Molecular Weight: 300.26288
• Mol File: 60325-08-8.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione(60325-08-8)
• EPA Substance Registry System: (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione(60325-08-8)

Safety Data

• Hazardous Substances Data: 60325-08-8(Hazardous Substances Data)

Usage

Description

(3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione is a complex chemical compound that belongs to the class of furocoumarins. It is a derivative of coumarin and is known for its potential therapeutic properties. (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione has a unique molecular structure that makes it of interest in pharmaceutical research for its potential medicinal applications.

Uses

Used in Pharmaceutical Research:
(3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione is used as a subject of pharmaceutical research for its potential therapeutic properties. Its complex molecular structure and potential medicinal applications make it a promising candidate for further study.
Used in Anti-inflammatory Applications:
Furocoumarins, including (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione, have been studied for their anti-inflammatory effects. (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione may be used as an anti-inflammatory agent to help reduce inflammation and alleviate symptoms associated with various inflammatory conditions.
Used in Anti-cancer Applications:
Furocoumarins have also been studied for their anti-cancer properties. (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione may be used as an anti-cancer agent to help inhibit the growth and spread of cancer cells.
Used in Phototoxic Applications:
Furocoumarins are known for their phototoxic effects, which can be utilized in various applications. (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione may be used in phototoxic applications to target and destroy harmful cells when exposed to specific wavelengths of light.
Further research is needed to fully understand the biological activities and potential therapeutic uses of (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione. Its complex molecular structure and potential applications make it a promising candidate for future pharmaceutical development.

Upstream product

• 1001438-91-0 (1S,3S)-3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-1H-naphtho[2,3-c]pyran-3-acetic acid 
• 88293-09-8 (1S,3S)-3,4,5,10-tetrahydro-9-hydroxy-3-(2-hydroxyethyl)-1-methyl-5,10-dioxo-1H-naphtho[2,3-c]pyran 
• 1001438-89-6 (1S,3S)-3,4,5,10-tetrahydro-3-(2-hydroxyethyl)-9-methoxy-1-methyl-5,10-dioxo-1H-naphtho[2,3-c]pyran 
• 1001438-86-3 (R)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-5,6-dihydro-4-methoxy-2H-pyran-2-one 
• 79383-44-1 methyl 2-methyl-6-methoxybenzoate 
• 1001438-87-4 (S)-3,4-dihydro-10-hydroxy-3-(2-(tert-butyldimethylsilyloxy)ethyl)-9-methoxy-1H-naphtho[2,3-c]pyran-1-one 
• 226213-84-9 epi-7-O-Methylkalafungin 
• 107941-22-0 2-bromo-1,4,5-trimethoxynaphthalene 
• 859234-21-2 (3aR,5S,11bR)-3,3a,5,11b-tetrahydro-6,7,11-trimethoxy-5-methyl-1,4-dioxacyclopent[a]anthracen-2-one 
• 859234-18-7 (4R,5R)-4-hydroxy-5-(1',4',5'-trimethoxynaphth-2'-yl)dihydrofuran-2(3H)-one 
• 859234-19-8 acetic acid 1-(1,4,5-trimethoxy-naphthalen-2-yl)-allyl ester 
• 859234-20-1 1-(1,4,5-trimethoxy-naphthalen-2-yl)-prop-2-en-1-ol 
• 859234-24-5 (3aS,5R,11bS)-6,7,11-trimethoxy-5-methyl-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromen-2-one 
• 859234-23-4 (4S,5S)-4-hydroxy-5-(1',4',5'-trimethoxynaphth-2'-yl)dihydrofuran-2(3H)-one 

Downstream Products

• 52934-83-5 4-deoxykalafunginic acid 

Relevant articles and documents

The divergent asymmetric synthesis of kalafungin, 5-epi-frenolicin B and related pyranonaphthoquinone antibiotics

A divergent, asymmetric method for the synthesis of pyranonaphthoquinones is reported. The synthetic strategy applies a Staunton-Weinreb annulation between substituted ortho-toluates and the (R)-pyran-2-one 7 to construct the key naphthopyranone intermediates. Stereoselective introduction of either a methyl or propyl C5 alkyl substituent by use of Grignard addition/silane- mediated reduction and a sequence of oxidations gave a series of pyranonaphthoquinones including kalafungin 1, 5-epi-9-methoxykalafungin 34 and 5-epi-frenolicin B 24.

Unexpected regioselectivity in the synthesis of pyranonaphthoquinone via the diels-alder reaction

The unusual regioselectivity In the Diels-Alder reactions of pyranoquinone 1 with (4,4-dlmethoxybuta-1,3-dlen-2-yloxy)trimethylsilane 2 are explored by both computations and experiments. The regioselectivity Is controlled by the electrostatic interaction of the lactone ring-oxygen and the vicinal quinone oxygen on the transition structure, which can be tuned by the terminal methyl group of the butadienes.

Efficient synthesis of (+)-kalafungin and (-)-nanaomycin D by asymmetric dihydroxylation, oxa-pictet-spengler cyclization, and H2SO 4-mediated isomerization

The pyranonaphthoquinone antibiotics and antitumor agents (+)-kalafungin (1) and (-)-nanaomycin D (3 = ent-1) were synthesized from 1,5-napthalenediol (13) in 11 steps. Stereocontrol was high: 99.5 ee/93% diastereoselectivity for 1, 98.5% ee/94% diastereoselectivity for 3. Enantiocontrol was achieved by the asymmetric dihydroxylation of the β,γ-unsaturated ester 9. Diastereocontrol was realized in the final step by an almost complete epimerization in H2SO4.