440369-05-1

Basic information

• Product Name: 1,4-Butanediol, 1-cyclohexyl-2-methyl-2-phenyl-, (1S,2S)-
• CAS NO: 440369-05-1
• Molecular Formula: C17H26O2
• Molecular Weight: 262.392
• Mol File: 440369-05-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,4-Butanediol, 1-cyclohexyl-2-methyl-2-phenyl-, (1S,2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Butanediol, 1-cyclohexyl-2-methyl-2-phenyl-, (1S,2S)-(440369-05-1)
• EPA Substance Registry System: 1,4-Butanediol, 1-cyclohexyl-2-methyl-2-phenyl-, (1S,2S)-(440369-05-1)

Safety Data

• Hazardous Substances Data: 440369-05-1(Hazardous Substances Data)

Upstream product

• 440369-02-8 (1S,2S)-2-methyl-1,2-diphenylbutane-1,4-diol 
• 54976-38-4 (E)-3-phenylbut-2-en-1-ol 
• 124604-57-5 [(1E)-3-chloro-1-methylprop-1-en-1-yl]benzene 
• 440369-00-6 ((E)-3-phenyl-2-butenyl)(trichloro)silane 
• 440369-01-7 (1S,2S)-2-methyl-1,2-diphenyl-3-buten-1-ol 
• 898528-32-0 3-methyl-3-phenyl-tetrahydro-furan-2-ol 
• 931-50-0 cyclohexylmagnesium bromide 

Downstream Products

• 440369-06-2 (2S)-4-cyclohexyl-4-oxo-3-methyl-3-phenylbutanal 
• 228418-82-4 (2S)-(+)-1-cyclohexyl-4-[4-(2-methoxyphenyl)-1-piperazinyl]-2-methyl-2-phenyl-1-butanone 

Relevant articles and documents

Regio- and stereoselective SN2′ reaction of an allylic picolinate in the synthesis of LY426965

Allylic substitution of secondary γ,γ-disubstituted allylic picolinates with ArMgBr-based copper reagents was applied to the synthesis of LY426965. Reduction of (R)-6-(PMB-oxy)-3-hexyn-2-ol of 93% ee (PMB = p-MeOC6H4CH2) using Red-Al gave (R,Z)-4-iodo-5-(PMB-oxy)hex-3-en-2-ol, which was later converted to the Me-substituted allylic picolinate by Pd-catalyzed coupling with MeZnI followed by esterification with picolinic acid. Allylic substitution with PhMgBr/Cu(acac)2 proceeded with high anti SN2′ selectivity (99%). Ozonolysis, addition of c-Hex-MgBr to the resulting aldehyde, and reductive amination with the piperazine derivative afforded LY426965.

Asymmetric Construction of Quaternary Centers by Enantioselective Allylation: Application to the Synthesis of the Serotonin Antagonist LY426965

(Matrix Presented) Catalytic enantioselective allylation with a chiral bisphosphoramide was applied to the synthesis of LY426965, a serotonin antagonist. The key step, addition of a 3,3-disubstituted allyltrichlorosilane to benzaldehyde, provided the addu