1606994-01-7

Basic information

• Product Name: (2R,3R)-2-((bis(4-methoxy-3,5-dimethylphenyl)methyl)amino)octadecane-1,3-diol
• Synonyms: (2R,3R)-2-((bis(4-methoxy-3,5-dimethylphenyl)methyl)amino)octadecane-1,3-diol
• CAS NO: 1606994-01-7
• Molecular Weight: 583.896
• Mol File: 1606994-01-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2R,3R)-2-((bis(4-methoxy-3,5-dimethylphenyl)methyl)amino)octadecane-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-2-((bis(4-methoxy-3,5-dimethylphenyl)methyl)amino)octadecane-1,3-diol(1606994-01-7)
• EPA Substance Registry System: (2R,3R)-2-((bis(4-methoxy-3,5-dimethylphenyl)methyl)amino)octadecane-1,3-diol(1606994-01-7)

Safety Data

• Hazardous Substances Data: 1606994-01-7(Hazardous Substances Data)

Upstream product

• 1072879-54-9 3,3',5,5'-tetramethyl-4,4'-dimethoxy benzhydrylamine 
• 1606994-02-8 ethyl (2S,3R)-2-((bis(4-methoxy-3,5-dimethylphenyl)methyl)amino)-3-hydroxyoctadecanoate 
• 629-80-1 n-hexadecylaldehyde 
• 1606993-91-2 ethyl (2S,3S)-1-(bis(4-methoxy-3,5-dimethylphenyl)methyl)-3-pentadecylaziridine-2-carboxylate 
• 36653-82-4 1-Hexadecanol 

Relevant articles and documents

Multicomponent cis- and trans-Aziridinatons in the Syntheses of All Four Stereoisomers of Sphinganine

All four stereoisomers of sphinganine can be synthesized by a multicomponent aziridination of an aldehyde, an amine and an α-diazo carbonyl compound mediated by a BOROX catalyst with high asymmetric induction (≥96% ee). The threo isomers are available from ring-opening of cis-aziridines by an oxygen nucleophile with inversion at the C-3 position and the erythro-isomers are likewise available from trans-aziridines.

A General Synthesis of Sphinganines through Multicomponent Catalytic Asymmetric Aziridination

A catalytic asymmetric synthesis of all four stereoisomers of sphinganine is described starting from hexadecanal. Utilizing either the (R) or (S) enantiomer of a BOROX catalyst, a multicomponent reaction of this aldehyde with an amine and ethyl diazoacetate gives rise to enantiomeric aziridine-2-carboxylates. Access to all diastereomers of sphinganine is realized upon ring opening of the enantiopure aziridine-2-carboxylate at the C-3 position by direct SN2 attack of an oxygen nucleophile, which occurs with inversion of configuration and by ring expansion of an N-acyl aziridine to an oxazolidinone and then hydrolysis. Overall, this process results in the formal ring opening of the aziridine with an oxygen nucleophile with retention of configuration.