127951-03-5

Basic information

• Product Name: (R)-4-[Benzyloxy-(3-methoxy-4-trimethylsilanyloxy-phenyl)-methyl]-dihydro-furan-2-one
• CAS NO: 127951-03-5
• Molecular Weight: 400.547
• Mol File: 127951-03-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (R)-4-[Benzyloxy-(3-methoxy-4-trimethylsilanyloxy-phenyl)-methyl]-dihydro-furan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-[Benzyloxy-(3-methoxy-4-trimethylsilanyloxy-phenyl)-methyl]-dihydro-furan-2-one(127951-03-5)
• EPA Substance Registry System: (R)-4-[Benzyloxy-(3-methoxy-4-trimethylsilanyloxy-phenyl)-methyl]-dihydro-furan-2-one(127951-03-5)

Safety Data

• Hazardous Substances Data: 127951-03-5(Hazardous Substances Data)

Upstream product

• 127951-00-2 (3R)-(+)-3-(4-Trimethylsiloxy-3-methoxybenzyl)butan-4-olide 
• 111266-00-3 (R)-4-<(4-hydroxy-3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 75-77-4 chloro-trimethyl-silane 
• 127951-01-3 (3R)-(6R,S)-(+)-3-(α-Benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 140193-24-4 (+/-)-3-<α-Bromo-4-(tertio-butyl dimethylsiloxy)-3-methoxybenzyl>butan-4-olide 
• 140193-23-3 (+/-)-3-<(4-Tertio-butyl dimethylsiloxy)-3-methoxybenzyl>butan-4-olide 
• 100-51-6 benzyl alcohol 
• 111194-04-8 3-methoxycarbonyl-4-(4-hydroxy-3-methoxyphenyl)butanoic acid 
• 127951-00-2 (+/-)-3-(4-Trimethylsiloxy-3-methoxybenzyl)butan-4-olide 
• 84755-40-8 (hydroxy-4 methoxy-3 benzyl)-4 dihydro-3H-furannone-2 
• 911805-41-9 (+/-)-3-(α-Benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 

Downstream Products

• 127951-04-6 (+/-)-2-(4-Benzyloxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 127951-04-6 4-[Benzyloxy-(4-hydroxy-3-methoxy-phenyl)-methyl]-3-(4-benzyloxy-3-methoxy-benzyl)-dihydro-furan-2-one 
• 127951-04-6 (2R,3R)-(6R,S)-(+)-2-(4-Benzyloxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 66748-86-5 (+/-)-α-conidendrin 
• 127951-05-7 4-[Benzyloxy-(4-hydroxy-3-methoxy-phenyl)-methyl]-3-(4-hydroxy-3-methoxy-benzyl)-dihydro-furan-2-one 
• 518-55-8 (+/-)-α-Conidendrine 
• 127951-05-7 (+/-)-2-(4-Hydroxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 5447-65-4 O-diacetyl-(+/-)-α-conidendrine 
• 25047-22-7 (-)-O-Diacetyl-α-conidendrine 
• 140193-27-7 (-)-O-6-Benzyl-α-conidendrine 
• 127951-05-7 (2R,3R)-(6R,S)-(+)-2-(4-Hydroxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 518-55-8 conidendrin 
• 27779-34-6 (-)-α-conidendrin 

Relevant articles and documents

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(-)-α-Conidendrin 1 was synthesized according to a general reactionscheme that could be applied to other retrolignans as well. Thus, treatment of the optically active β-benzyl-γ-butyrolactone (R)-(+)-4 with NBS, followed with benzyl alcohol, selectively introduced a benzyloxy group in the benzylic position and afforded the mixture of epimers 7. α-Alkylation of the lithium enolate of the corresponding silyl ethers 10, with O-benzylvanillyl bromide 11, gave the trans disubstituted lactones 13 (2 epimers). Catalytic hydrogenolysis (Pd-C) of 13 selectively split the aryl benzyl ether linkage, and gave the compounds 14. Intramolecular Friedel-Crafts cyclization of the latter, using the benzyloxy group as the leaving group, was induced with BF3-Et2O and afforded (-)-α-conidendrin 1 in 36% overall yield from methyl α-vanillylhemis uccinate (R)-(+)-17.