6302-93-8

Usage

InChI:InChI=1/C20H16O2S2/c1-3-7-16(8-4-1)23-20(24-17-9-5-2-6-10-17)15-11-12-18-19(13-15)22-14-21-18/h1-13,20H,14H2

Upstream product

• 120-57-0 piperonal 
• 108-98-5 thiophenol 
• 882-33-7 diphenyldisulfane 
• 103844-12-8 erythro-3-<3'',4''-dimethoxy-α,α-bis(phenylthio)benzyl>-2-(α-hydroxy-3',4'-methylenedioxybenzyl)-γ-butyrolactone 
• 495-76-1 piperonol 

Downstream Products

• 140138-37-0 (-)-(3S,4R,5R)-3-(3',4',5'-trimethoxybenzyl)-4-<3'',4''-methylenedioxy-α,α-bis(phenylthio)benzyl>-5-(1-menthyloxy)butyrolactone 
• 135965-91-2 (-)-(4R,5R)-4-<3',4'-methylenedioxy-α,α-bis(phenylthio)benzyl>-5-(1-menthyloxy)butyrolactone 
• 120040-64-4 (+)-(2S,3S,4R)-2-(Benzyloxy)-4-<3,4-(methylenedioxy)benzoyl>-3-<<3,4-(methylenedioxy)phenyl>bis(phenylthio)methyl>tetrahydrofuran 
• 78473-72-0 3-(3,4-dimethoxybenzyl)-4-<3,4-methylenedioxy-α,α-bis(phenylthio)behzyl>butyrolactone 
• 118825-99-3 2-(α-hydroxy-3',4',5'-trimethoxybenzyl)-3-<3'',4''-methylenedioxy-α,α-bis(phenylthio)benzyl>-γ-butyrolactone 
• 140160-51-6 (-)-(3S,4R,5R,6R)-3-(3',4',5'-trimethoxy-α-hydroxybenzyl)-4-<3'',4''-methylenedioxy-α,α-bis(phenylthio)benzyl>-5-(1-menthyloxy)butyrolactone 
• 85352-32-5 α-phenylthio-1,3-benzodioxole-5-acetonitrile 
• 158665-02-2 (3R,4R,5R)-3-(1,3-Benzodioxol-5-ylmethyl)-4-<(1,3-benzodioxol-5-yl)bis(phenylthio)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone 
• 158665-03-3 (3R,4R,5R)-4-<1,3-Benzodioxol-5-ylbis(phenylthio)methyl>-3-<(4-(benzyloxy)-3-methoxyphenyl)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone 
• 220597-13-7 Acetic acid (2R,3R)-3-(benzo[1,3]dioxol-5-yl-bis-phenylsulfanyl-methyl)-5-oxo-tetrahydro-furan-2-yl ester 
• 28115-68-6 (-)-Pluviatolide 
• 158705-72-7 (3R,4R)-4-(1,3-Benzodioxol-5-ylmethyl)-3-<(4-(benzyloxy)-3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 26543-89-5 (-)-hinokinin 
• 120040-66-6 (-)-(2S,3R,4R)-2-(Benzyloxy)-4-<3,4-(methylenedioxy)benzoyl>-3-<3,4-(methylenedioxy)benzyl>tetrahydrofuran 

Relevant academic research and scientific papers

Dithioacetalization or thioetherification of benzyl alcohols using 9-mesityl-10-methylacridinium perchlorate photocatalyst

We report herein the use of 9-mesityl-10-methylacridinium perchlorate as the visible-light photocatalyst for dithioacetalization or thioetherification of benzyl alcohols in one pot using aerial dioxygen as a terminal oxidant. EPR analysis and Stern-Volmer

Enantioselective synthesis of benzylbutyrolactones from 5-hydroxyfuran-2(5H)-one. New chiral synthons for dibenzylbutyrolactone lignans by a chemoenzymatic route

A chemoenzymatic method is described for the asymmetric synthesis of benzylbutyrolactones. (R)-5-Acetoxyfuran-2(5H)-one (12) was obtained with ee > 99% in a multigram scale catalytic esterification using immobilized lipase PS. The addition of lithiated dithianes to chiral synthon 12 was followed by an effective multistep reduction to produce enantiomerically pure benzylbutyrolactones.

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.

General Conjugate-Addition Method for the Synthesis of Enantiomerically Pure Lignans. Total Synthesis of (-)- and (+)-Burseran, (-)-Dehydroxycubebin, (-)-Trichostin, (-)-Cubebin, (-)-5''-Methoxyhinokinin, and (-)-Hinokinin

Conjugate addition of benzylic diphenyldithioacetal anions to enantiomerically pure (-)-(2R)-and (+)-(2S)-(benzyloxy)-2,5-dihydro-4-furan (2 r and 2 s) gave complete lignan skeletons of the dibenzylbutane class.Desulfurization followed by hydrogenolysis and, when appropriate, oxidation gave the title enantiomerically pure > 99 percent ee) lignans 45 - 50 in 24 - 35 percent overall yields from 2 r and 2 s.

PREPARATION OF N-ALKADIENYL N-E-2-ARYLETHENYLCARBAMATES VIA SULFOXIDE ELIMINATION IN A SYNTHETIC APPROACH TO LYCORINE

N-E-2-Arylethenylcarbamates have been prepared in good yields from N-carbamates via sulfoxide elimination towards nitrogen.

SYNTHESIS OF LIGNANS RELATED TO THE PODOPHYLLOTOXIN SERIES

The dibenzyl-γ-butyrolactone derivative (6), readily prepared by tandem conjugate addition to but-2-en-4-olide, undergoes cyclisation with trifluoroacetic acid to afford retrochinensin (10).After desulphurisation of (6) with Raney nickel, cyclisation yields the aryltetralin lactone (9).Treatment of (6) with concentrated perchloric acid gives a quantitative yield of the rearranged compound (11), which after appropriate modification can be cyclised to afford either the retro-dihydroarylnaphthalene lactone (13), or the 4-substituted aryltetralin lactone (15).Extension of this approach to a second dibenzylbutyrolactone derivative (21) leads to the retro-dihydroarylnaphthalene lactone (25), but gives only a low yield of the required podophyllotoxin derivative (27).