133644-85-6

Basic information

• Product Name: (2S,3R,4R)-3-hydroxymethyl-4-(3,4-methylenedioxybenzyl)-2-(3,4-methylenedioxyphenyl)tetrahydrofuran
• CAS NO: 133644-85-6
• Molecular Weight: 356.375
• Mol File: 133644-85-6.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: (2S,3R,4R)-3-hydroxymethyl-4-(3,4-methylenedioxybenzyl)-2-(3,4-methylenedioxyphenyl)tetrahydrofuran(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4R)-3-hydroxymethyl-4-(3,4-methylenedioxybenzyl)-2-(3,4-methylenedioxyphenyl)tetrahydrofuran(133644-85-6)
• EPA Substance Registry System: (2S,3R,4R)-3-hydroxymethyl-4-(3,4-methylenedioxybenzyl)-2-(3,4-methylenedioxyphenyl)tetrahydrofuran(133644-85-6)

Safety Data

• Hazardous Substances Data: 133644-85-6(Hazardous Substances Data)

Upstream product

• 16108-37-5 trans-4-hydroxymethyl-5-(3,4-methylenedioxyphenyl)-dihydrofuran-2(3H)-one 
• 128791-84-4 (4S,5R)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-trimethylsilanyl-dihydro-furan-2-one 
• 120-57-0 piperonal 
• 128791-86-6 (3R,4S,5R)-5-Benzo[1,3]dioxol-5-yl-3-benzo[1,3]dioxol-5-ylmethyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-dihydro-furan-2-one 
• 58095-76-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-ol 
• 59901-91-6 3-(3,4-methylenedioxyphenyl)-3-hydroxy-1,2-epoxypropane 
• 67911-75-5 (E)-5-(3-bromoprop-1-en-1-yl)benzo[d][1,3]dioxole 
• 438581-64-7 1-(3,4-methylenedioxyphenyl)-1-(3-(3,4-methylenedioxyphenyl)-2-propenyloxy)-2,3-epoxypropane 
• 128791-84-4 4β-(tert-butyldimethylsilyloxymethyl)-5β-(3,4-methylenedioxyphenyl)-3α-trimethylsilyldihydrofuran-2(3H)-one 
• 16108-37-5 cis-4-hydroxymethyl-5-(3,4-methylenedioxyphenyl)dihydrofuran-2(3H)-one 
• 62848-90-2 cis-4-carboxy-5-(3,4-methylenedioxyphenyl)dihydrofuran-2(3H)-one 
• 128791-86-6 4β-tert-butyldimethylsilyloxymethyl-3β-(3,4-methylenedioxybenzyl)-5β-(3,4-methylenedioxyphenyl)dihydrofuran-2(3H)-one 
• 141-78-6 ethyl acetate 
• 133-03-9 sesamin 

Relevant articles and documents

LIGNANDS FROM NECTANDRA TURBACENSIS

Bark and wood of Nectanandra turbacensis (Lauraceae) contain, besides the known furofuran lignands (+)-sesamin, (+)-demethoxyexcelsin and (+)-piperitol, the novel (1R,5R,2S,6S)-2-(3'-methoxy-4',5'-methylenedioxyphenyl)-6-(4"-hydroxy-3"-methoxyphenyl)-3,7-dioxabicyclooctane and (1R,2S,5R)-2-(3'-methoxy-4',5'-methylenedioxyphenyl)-3,7-dioxa-6-oxobicyclooctane. Key Word Index--Nectandra turbacensis; Lauraceae; furofuran lignands; 2-aryl-3,7-dioxa-6-oxobicyclooctane

A sterically encumbered photoredox catalyst enables the unified synthesis of the classical lignan family of natural products

Herein, we detail a unified synthetic approach to the classical lignan family of natural products that hinges on divergence from a common intermediate that was strategically identified from nature's biosynthetic blueprints. Efforts toward accessing the common intermediate through a convergent and modular approach resulted in the discovery of a sterically encumbered photoredox catalyst that can selectively generate carbonyl ylides from electron-rich epoxides. These can undergo concerted [3 + 2] dipolar cycloadditions to afford tetrahydrofurans, which were advanced (2-4 steps) to at least one representative natural product or natural product scaffold within all six subtypes in classical lignans. The application of those synthetic blueprints to the synthesis of heterolignans bearing unnatural functionality was demonstrated, which establishes the potential of this strategy to accelerate structure-activity-relationship studies of these natural product frameworks and their rich biological activity.

Reagent-controlled stereoselective synthesis of lignan-related tetrahydrofurans

The reaction of ring-closing metathesis-derived cyclic allylsiloxanes 3 with aldehydes in the presence of a Lewis acid gives 2,3,4-trisubstituted tetrahydrofurans related to the furanolignan family of natural products. The reactions proceed with complete