651779-99-6

Basic information

• Product Name: (1R,2R,5R,6S)-2-(4-methanesulfonyloxy-3-methoxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octane
• Synonyms: (1R,2R,5R,6S)-2-(4-methanesulfonyloxy-3-methoxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octane
• CAS NO: 651779-99-6
• Molecular Weight: 514.574
• Mol File: 651779-99-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,2R,5R,6S)-2-(4-methanesulfonyloxy-3-methoxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,5R,6S)-2-(4-methanesulfonyloxy-3-methoxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octane(651779-99-6)
• EPA Substance Registry System: (1R,2R,5R,6S)-2-(4-methanesulfonyloxy-3-methoxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octane(651779-99-6)

Safety Data

• Hazardous Substances Data: 651779-99-6(Hazardous Substances Data)

Upstream product

• 651779-95-2 (4R,5S)-5-(4-methanesulfonyloxy-3-methoxy)phenyl-3-diazo-4-{[(4-methanesulfonyloxy-3-methoxybenzyl)oxy]methyl}tetrahydro-2-furanone 
• 651779-94-1 (4R,5S)-5-(4-methanesulfonyloxy-3-methoxy)phenyl-4-{[(4-methanesulfonyloxy-3-methoxybenzyl)oxy]methyl}-3-acetyltetrahydro-2-furanone 
• 651779-96-3 (1S,2R,5R,6S)-2-(4-methanesulfonyloxy-3-methoxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octan-8-one 
• 52200-05-2 4-methanesulfonyloxy-3-methoxybenzaldehyde 
• 651779-97-4 (2R,3R,4S)-2-[(4-methanesulfonyloxy-3-methoxy)phenyl]-3-hydroxymethyl-4-{[(4-methanesulfonyloxy-3-methoxy)phenyl](hydroxy)methyl}tetrahydrofuran 
• 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 
• 651779-84-9 1-(4-methanesulfonyloxy-3-methoxyphenyl)prop-2-en-1-ol 
• 651779-83-8 (1S)-1-(4-methanesulfonyloxy-3-methoxyphenyl)prop-2-en-1-ol 

Downstream Products

• 487-36-5 (+)-epipinoresinol 
• 60102-89-8 (+)-epipinoresinol dimethyl ether 

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.