28071-34-3

Basic information

• Product Name: 3-Furanmethanol,2-(1,3-benzodioxol-5-yl)-4-(1,3-benzodioxol-5-ylmethyl)tetrahydro- (9CI)
• Synonyms: 3-Furanmethanol,tetrahydro-2-[3,4-(methylenedioxy)phenyl]-4-piperonyl- (8CI); Dihydrosesamin;Sesamin, dihydro-
• CAS NO: 28071-34-3
• Molecular Formula: C20H20 O6
• Molecular Weight: 356.375
• Mol File: 28071-34-3.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 3-Furanmethanol,2-(1,3-benzodioxol-5-yl)-4-(1,3-benzodioxol-5-ylmethyl)tetrahydro- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Furanmethanol,2-(1,3-benzodioxol-5-yl)-4-(1,3-benzodioxol-5-ylmethyl)tetrahydro- (9CI)(28071-34-3)
• EPA Substance Registry System: 3-Furanmethanol,2-(1,3-benzodioxol-5-yl)-4-(1,3-benzodioxol-5-ylmethyl)tetrahydro- (9CI)(28071-34-3)

Safety Data

• Hazardous Substances Data: 28071-34-3(Hazardous Substances Data)

Upstream product

• 438581-64-7 1-(3,4-methylenedioxyphenyl)-1-(3-(3,4-methylenedioxyphenyl)-2-propenyloxy)-2,3-epoxypropane 
• 62096-66-6 4β-hydroxymethyl-3α-(3,4-methylenedioxybenzyl)-5α-(3,4-methylenedioxyphenyl)dihydrofuran-2(3H)-one 
• 16108-37-5 trans-4-hydroxymethyl-5-(3,4-methylenedioxyphenyl)-dihydrofuran-2(3H)-one 
• 140860-60-2 trans-4-hydroxymethyl-5-(3,4-methylenedioxyphenyl)-3E-(3,4-methylenedioxybenzylidene)dihydrofuran-2(3H)-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 
• 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 
• 128791-85-5 4β-tert-butyldimethylsilyloxymethyl-5β-(3,4-methylenedioxyphenyl)-3E-(3,4-methylenedioxybenzylidene)dihydrofuran-2(3H)-one 
• 128791-83-3 (4R,5R)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-dimethyl-silanyloxymethyl)-dihydro-furan-2-one 

Relevant articles and documents

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

Stereoselective synthesis of trisubstituted tetrahydrofurans by radical cyclisation reaction using a hypophosphite salt. Application to the total synthesis of (±)-dihydrosesamin

The stereoselective synthesis of tetrahydrofurans has been achieved from bromoalkynes and bromoalkenes by intramolecular radical cyclisation using a hypophosphite salt. This radical cyclisation strategy has successfully been applied to the total synthesis