1356336-74-7

Basic information

• Product Name: (1S)-1-[3,4-dimethoxy-2-(S)-p-tolylsulfinyl]benzyl-6,7-dimethoxy-2-(S)-p-tolylsulfinyl-1,2,3,4-tetrahydroisoquinoline
• Synonyms: (1S)-1-[3,4-dimethoxy-2-(S)-p-tolylsulfinyl]benzyl-6,7-dimethoxy-2-(S)-p-tolylsulfinyl-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 1356336-74-7
• Molecular Weight: 619.803
• Mol File: 1356336-74-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S)-1-[3,4-dimethoxy-2-(S)-p-tolylsulfinyl]benzyl-6,7-dimethoxy-2-(S)-p-tolylsulfinyl-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-1-[3,4-dimethoxy-2-(S)-p-tolylsulfinyl]benzyl-6,7-dimethoxy-2-(S)-p-tolylsulfinyl-1,2,3,4-tetrahydroisoquinoline(1356336-74-7)
• EPA Substance Registry System: (1S)-1-[3,4-dimethoxy-2-(S)-p-tolylsulfinyl]benzyl-6,7-dimethoxy-2-(S)-p-tolylsulfinyl-1,2,3,4-tetrahydroisoquinoline(1356336-74-7)

Safety Data

• Hazardous Substances Data: 1356336-74-7(Hazardous Substances Data)

Upstream product

• 1356336-70-3 (S)-1,2-dimethoxy-4-methyl-3-(p-tolylsulfinyl)benzene 
• 1356336-71-4 (S)-1-[3,4-dimethoxy-2-(p-tolylsulfinyl)phenyl]-N,N-dimethylmethanamine 
• 1356336-72-5 (S)-1-(chloromethyl)-3,4-dimethoxy-2-(p-tolylsulfinyl)benzene 
• 65495-21-8 N,N-dimethyl-3,4-dimethoxybenzylamine 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 

Downstream Products

• 1356336-78-1 (1S)-1-(3,4-dimethoxy-2-(S)-(p-tolylsulfinyl)benzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 483-14-7 tetrahydropalmatine 

Relevant articles and documents

Asymmetric synthesis of (S)-(-)-tetrahydropalmatine and (S)-(-)-canadine via a sulfinyl-directed Pictet-Spengler cyclization

(S)-(-)-Tetrahydropalmatine 2 and (S)-(-)-canadine 4 were synthesized in three steps from (S)-6, in 33% and 34% overall yield, respectively. Thus, condensation of the (S)-(E)-sulfinylimines 10 and 11 with the carbanion derived from (S)-6 gave the tetrahydroisoquinolines 12 and 13, respectively, which upon TFA induced N-desulfinylation, and subsequent microwave assisted Pictet-Spengler cyclization effected both cyclization and C-desulfinylation producing (S)-(-)-tetrahydropalmatine 2 and (S)-(-)-canadine 4 in optically pure form.