96995-00-5

Basic information

• Product Name: 3-benzyloxybenzaldehyde bis(phenylthio) acetal
• Synonyms: 3-benzyloxybenzaldehyde bis(phenylthio) acetal
• CAS NO: 96995-00-5
• Molecular Weight: 414.592
• Mol File: 96995-00-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-benzyloxybenzaldehyde bis(phenylthio) acetal(CAS DataBase Reference)
• NIST Chemistry Reference: 3-benzyloxybenzaldehyde bis(phenylthio) acetal(96995-00-5)
• EPA Substance Registry System: 3-benzyloxybenzaldehyde bis(phenylthio) acetal(96995-00-5)

Safety Data

• Hazardous Substances Data: 96995-00-5(Hazardous Substances Data)

Upstream product

• 1700-37-4 3-Benzyloxybenzaldehyde 
• 108-98-5 thiophenol 

Downstream Products

• 96995-01-6 (+/-)-trans-2-(3-benzyloxybenzyl)-3-<3-benzyloxy-α,α-bis(phenylthio)benzyl>butyrolactone 
• 96995-02-7 (+/-)-trans-<4,4-(2)H2>-2-(3-benzyloxybenzyl)-3-<3-benzyloxy-α,α-bis(phenylthio)>benzylbutyrolactone 
• 96995-03-8 <1,1-(2)H2>-(+/-)-2,3-bis-(3-hydroxybenzyl)butane-1,4-diol 
• 96998-65-1 <4,4-(2)H2>-(+/-)-trans-2,3-bis-(3-hydroxybenzyl)butyrolactone 
• 158705-71-6 (3R,4R)-3,4-Bis<(3-(benzyloxy)phenyl)methyl>dihydro-2(3H)-furanone 
• 76543-15-2 (-)-enterolactone 
• 76543-16-3 2,3-bis(3-hydroxybenzyl)-butane-1,4-diol 
• 158665-01-1 (3R,4R,5R)-3-<(3-(3-Benzyloxy)phenyl)methyl>-4-<(3-(benzyloxy)phenyl)bis(phenylthio)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone 

Relevant articles and documents

Enantioselective synthesis of natural dibenzylbutyrolactone lignans (-)-enterolactone, (-)-hinokinin, (-)-pluviatolide, (-)-enterodiol, and furofuran lignan (-)-eudesmin via tandem conjugate addition to γ-alkoxybutenolides1,2

A general and efficient method is described for the asymmetric synthesis of a variety of liguans. 5-(Menthyloxy)-2(5H)-furanones 5 proved to be excellent chiral synthons in this respect and could be transformed with complete stereoselectivity into a number of lignans. The addition of lithiated dithianes 7 to enantiomerically pure butenolides 5 was followed by quenching of the resulting lactone enolate anions with a benzylbromide (9) or with an aldehyde (6). This tandem addition quenching procedure gave the diastereomerically pure adducts 11, 26, or 27 in 50-67% yield, with a carbon skeleton as found in most natural lignans. As examples of the wide applicability of this method, the syntheses of the enantiomerically pure natural lignans (-)-hinokinin (23b), (-)-enterolactone (24a), (-)-pluviatolide (24c), and (-)-enterodiol (25) in overall yields of 29-37% from 5a and (-)eudesmin (30) in 16% overall yield from 5b are described.