28115-67-5

Basic information

• Product Name: 4-[(1S,3aα,6aα)-4α-(1,3-Benzodioxol-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan-1β-yl]-2-methoxyphenol
• Synonyms: 4-[(1S,3aα,6aα)-4α-(1,3-Benzodioxol-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan-1β-yl]-2-methoxyphenol;Pluviatilol
• CAS NO: 28115-67-5
• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.3692
• Mol File: 28115-67-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-[(1S,3aα,6aα)-4α-(1,3-Benzodioxol-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan-1β-yl]-2-methoxyphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(1S,3aα,6aα)-4α-(1,3-Benzodioxol-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan-1β-yl]-2-methoxyphenol(28115-67-5)
• EPA Substance Registry System: 4-[(1S,3aα,6aα)-4α-(1,3-Benzodioxol-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan-1β-yl]-2-methoxyphenol(28115-67-5)

Safety Data

• Hazardous Substances Data: 28115-67-5(Hazardous Substances Data)

Upstream product

• 105602-51-5 (+/-)-benzylpluviatilol 
• 120-57-0 piperonal 
• 62848-90-2 trans-4-carboxy-5-(3,4-methylenedioxyphenyl)dihydrofuran-2(3H)-one 
• 105602-54-8 (4S,5R)-5-Benzo[1,3]dioxol-5-yl-4-[(4-benzyloxy-3-methoxy-phenyl)-methoxy-methoxymethyl]-dihydro-furan-2-one 
• 105602-53-7 benzyl 2-epistyraxin 
• 651779-88-3 (4R,5S)-5-(4-methanesulfonyloxy-3-methoxy)phenyl-4-{[(3,4-methylenedioxybenzyl)oxy]methyl}-3-acetyltetrahydro-2-furanone 
• 651779-89-4 (4R,5S)-5-(4-methanesulfonyloxy-3-methoxy)phenyl-3-diazo-4-{[(3,4-methylenedioxybenzyl)oxy]methyl}tetrahydro-2-furanone 
• 651779-90-7 (1S,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octan-8-one 
• 651779-92-9 (1S,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octan-8-ol 
• 651779-87-2 (1R,4S,5S)-1-acetyl-4-(4-methanesulfonyloxy-3-methoxyphenyl)-3-oxabicyclo[3.1.0]hexan-2-one 
• 651779-86-1 (1S)-1-(4-methanesulfonyloxy-3-methoxyphenyl)allyl acetoacetate 
• 52200-05-2 4-methanesulfonyloxy-3-methoxybenzaldehyde 
• 651779-93-0 (1R,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octane 
• 16108-37-5 trans-4-hydroxymethyl-5-(3,4-methylenedioxyphenyl)-dihydrofuran-2(3H)-one 

Downstream Products

• 28115-69-7 (1R,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(3,4-dimethoxy)phenyl-3,7-dioxabicyclo[3.3.0]octane 

Relevant articles and documents

A Versatile Stereoselective Synthesis of endo,exo-Furofuranones: Application to the Enantioselective Synthesis of Furofuran Lignans

A new stereoselective route to endo,exo-2,6-diarylfurofuranones has been developed using Mn(III)-mediated intramolecular cyclopropanation and C-H insertion reactions as key C-C bond-forming steps. Mn(III)-mediated oxidative cyclization of acetoacetate derivative 11 afforded 1-acetyl-4-aryl-3-oxabicyclo[3.1.0]hexan-2-one (12) with excellent diastereocontrol (d.r. 22:1). Subsequent Lewis acid-catalyzed opening of the activated cyclopropane ring present in 12 with benzylic alcohols then gave α-acetyl-γ-butyrolactones 16 and 18-20, which reacted efficiently with in situ-generated TfN3 to secure the key α-diazo-γ -butyrolactones 22-25. Highly stereoselective rhodium-catalyzed C-H insertion reactions of diazolactones 22-25 completed the synthesis of endo,exo-2,6-diarylfurofuranones 26-29 in overall yields ranging from 41 to 48% from 1-phenylallyl alcohol (±)-10. The approach developed for the furofuranones 26-29 was then applied to the asymmetric syntheses of four furofuran lignans, (+)-xanthoxylol (1), (+)-methylxanthoxylol (2), (+)-epipinoresinol (3), and (+)-epieudesmin (4), starting from enantiomerically enriched 1-arylallyl alcohol (S)-31.

Synthetic methods for (Exo,Exo)- and (Exo-,Endo)-2,6-diarylbicyclo[3:3:0]octane lignans: Syntheses of (±)-aptosimon, (±)-styraxin, (±)-asarinin, and (±)-pluviatilol

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