482351-14-4

Basic information

• Product Name: (5R,6R)-6-hydroxymethyl-5-[(1E)-3-[(4-methoxyphenyl)methoxy]-1-[[[tris-(1-methylethyl)silyl]oxy]methyl]-1-propenyl]-2-(2-nitrophenyl)-2-cyclohexen-1-one
• Synonyms: (5R,6R)-6-hydroxymethyl-5-[(1E)-3-[(4-methoxyphenyl)methoxy]-1-[[[tris-(1-methylethyl)silyl]oxy]methyl]-1-propenyl]-2-(2-nitrophenyl)-2-cyclohexen-1-one
• CAS NO: 482351-14-4
• Molecular Weight: 609.835
• Mol File: 482351-14-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (5R,6R)-6-hydroxymethyl-5-[(1E)-3-[(4-methoxyphenyl)methoxy]-1-[[[tris-(1-methylethyl)silyl]oxy]methyl]-1-propenyl]-2-(2-nitrophenyl)-2-cyclohexen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5R,6R)-6-hydroxymethyl-5-[(1E)-3-[(4-methoxyphenyl)methoxy]-1-[[[tris-(1-methylethyl)silyl]oxy]methyl]-1-propenyl]-2-(2-nitrophenyl)-2-cyclohexen-1-one(482351-14-4)
• EPA Substance Registry System: (5R,6R)-6-hydroxymethyl-5-[(1E)-3-[(4-methoxyphenyl)methoxy]-1-[[[tris-(1-methylethyl)silyl]oxy]methyl]-1-propenyl]-2-(2-nitrophenyl)-2-cyclohexen-1-one(482351-14-4)

Safety Data

• Hazardous Substances Data: 482351-14-4(Hazardous Substances Data)

Upstream product

• 482351-12-2 (5R,6R)-6-hydroxymethyl-5-[(1E)-3-[(4-methoxyphenyl)methoxy]-1-[[[tris-(1-methylethyl)silyl]oxy]methyl]-1-propenyl]-2-cyclohexen-1-one 
• 482351-10-0 (3R)-3-[(1E)-3-[(4-methoxyphenyl)methoxy]-1-[[[tris-(1-methylethyl)silyl]oxy]methyl]-1-propenyl]cyclohexanone 
• 76074-18-5 trimethyl-(2-nitro-phenyl)-stannane 
• 482351-13-3 (5R,6R)-6-hydroxymethyl-2-iodo-5-[(1E)-3-[(4-methoxyphenyl)methoxy]-1-[[[tris-(1-methylethyl)silyl]oxy]methyl]-1-propenyl]-2-cyclohexen-1-one 

Downstream Products

• 509-40-0 diaboline 
• 482351-07-5 (5R,6R)-5-[(1E)-1-(hydroxymethyl)-3-[(4-methoxyphenyl)methoxy]-1-propenyl]-2-(2-nitrophenyl)-6-[[[2-(trimethylsilyl)ethoxy]methoxy]methyl]-2-cyclohexen-1-one 
• 482351-15-5 (6R,16α,19E)-1,2,19,20-tetradehydro-6-(ethylthio)-18-[(4-methoxyphenyl)methoxy]-17-[[2-(trimethylsilyl)ethoxy]methoxy]curan 
• 482351-05-3 (6R,16α,19E)-19,20-didehydro-6-(ethylthio)-18-[(4-methoxyphenyl)methoxy]-17-[[2-(trimethylsilyl)ethoxy]methoxy]curan 
• 482351-06-4 (1S,4E,5R,6R)-2-[2,2-bis(ethylthio)ethyl]-2,3,4,5,6,7-hexahydro-4-[2-[(4-methoxyphenyl)methoxy]ethylidene]-6-[[[2-(trimethylsilyl)ethoxy]methoxy]methyl]-1,5-methano-1H-azocino[4,3-b]indole 
• 1027259-59-1 (5R,6R)-5-[(E)-1-[(2,2-Bis-ethylsulfanyl-ethylamino)-methyl]-3-(4-methoxy-benzyloxy)-propenyl]-2-(2-nitro-phenyl)-6-(2-trimethylsilanyl-ethoxymethoxymethyl)-cyclohex-2-enone 
• 482351-31-5 C₃₅H₅₀N₂O₄SSi 
• 793724-08-0 C₂₉H₃₆N₂O₃S(C₂H₂O) 
• 482351-22-4 (5R,6R)-5-[(1E)-3-[(4-methoxyphenyl)methoxy]-1-[[[tris-(1-methylethyl)silyl]oxy]methyl]-1-propenyl]-2-(2-nitrophenyl)-6-[[[2-(trimethylsilyl)ethoxy]methoxy]methyl]-2-cyclohexen-1-one 

Relevant articles and documents

Enantioselective total synthesis of (-)-strychnine: Development of a highly practical catalytic asymmetric carbon-carbon bond formation and domino cyclization

An enantioselective total synthesis of (-)-strychnine was accomplished through the use of the highly practical catalytic asymmetric Michael reaction (0.1 mol% of (R)-ALB, greater than kilogram scale, without chromatography, 91% yield and >99% ee), and a domino cyclization that simultaneously constructed the B- and D- rings of strychnine (>77% yield). Newly-developed reaction conditions for thionium ion cyclization, NaBH3CN reduction of the imine moiety in the presence of a Lewis acid to prevent the ring-opening reaction, and chemoselective reduction of the thioether (desulfurization) in the presence of exocyclic olefin were pivotal to complete the synthesis. The described chemistry paves the way for the synthesis of more advanced Strychnos alkaloids. Graphical Abstract.