921202-50-8

Basic information

• Product Name: 3-Pyrrolidinol, 2-ethenyl-4-octyl-1-(phenylmethyl)-, (2S,3R,4S)-
• CAS NO: 921202-50-8
• Molecular Formula: C21H33NO
• Molecular Weight: 315.499
• Mol File: 921202-50-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-Pyrrolidinol, 2-ethenyl-4-octyl-1-(phenylmethyl)-, (2S,3R,4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyrrolidinol, 2-ethenyl-4-octyl-1-(phenylmethyl)-, (2S,3R,4S)-(921202-50-8)
• EPA Substance Registry System: 3-Pyrrolidinol, 2-ethenyl-4-octyl-1-(phenylmethyl)-, (2S,3R,4S)-(921202-50-8)

Safety Data

• Hazardous Substances Data: 921202-50-8(Hazardous Substances Data)

Upstream product

• 921202-36-0 C₁₃H₁₅NO 
• 3314-49-6 octyllithium 

Downstream Products

• 921202-60-0 (2S,3R,4S)-1-benzyl-2-(hydroxymethyl)-4-octylpyrrolidin-3-ol 
• 1167430-12-7 (3R,4S)-1-benzyl-4-octylpyrrolidin-3-ol 
• 1167430-15-0 (2S,3R,4S)-1-benzyl-3-(benzyloxy)-4-octyl-2-vinylpyrrolidine 

Relevant articles and documents

Highly regioselective oxirane ring-opening of a versatile epoxypyrrolidine precursor of new imino-sugar-based sphingolipid mimics

An in-depth study of the oxirane ring-opening reaction of a pivotal epoxypyrrolidine is reported. The introduction of various carbon- and heteroatom-centered nucleophiles at C4 has been achieved with high regiocontrol. The structures of the major products were assigned on the basis on an X-ray crystallographic study of six examples. A mechanistic study carried out at the B3LYP/6-31G** level of theory suggested that the steric control of the vinyl substituent was responsible for the regioselectivity. Finally, this approach was used to design and prepare imino-sugar-based sphingolipid mimics. A highly cytotoxic C-octylpyrrolidine is described. This compound was shown to interfere with the metabolism of sphing-olipids in murine melanoma cells, notably in inhibiting the production of glucosylceramide. Wiley-VCH Verlag GmbH & Co. KGaA.