Attention:

Certain features of Sigma-Aldrich.com will be down for maintenance the evening of Friday August 18th starting at 8:00 pm CDT until Saturday August 19th at 12:01 pm CDT.   Please note that you still have telephone and email access to our local offices. We apologize for any inconvenience.

The Next Generation of Labeled Synthons

By: Mike Willis, Chemfiles Volume 10 Article 4

Dr. Rodolfo Martinez and his group at Highlands Stable Isotopes have developed a novel set of patented stable isotope synthetic reagents. These exclusive reagents facilitate the production of site-specific and stereospecific labeled compounds. They also help improve the speed and quality of the synthesis of labeled materials. These versatile reagents include the following categories:

  • Protected methyl addition reagents
  • α-Keto amide, acid, and ester precursors
  • Olefi nation reagents
  • Phenyl vinyl compounds
  • Thioethers and dithioethers
  • Phthalimides and succinimides

Some of the most versatile compounds in the collection include the methyl additionreagents of which methyl-13C phenyl sulfide (716081) is a notable example. Methyl phenyl sulfide has a rich chemistry and, if prepared with carbon and deuterium labels in the methyl group, is a versatile labeling precursor easily converted into a nucleophilic or an electrophilic synthon.

Labeled methyl phenyl sulfide can be oxidized, adjusting the pKa and allowing for subsequent modifications. A Raney® Ni mediated desulfurization can be used to remove the sulfur, leaving a labeled methylene group. Alternatively, a 13C-labeled aldehyde, carboxylic acid, or carboxylic ester can be prepared directly.

back to top

Materials

     

References

  1. Martinez, R. A.; Alvarez, M. A.; Velarde, S. P.; Silks, L. A. P.; Stotter, P. L.; Schmidt, J. G.; Unkefer, C. J. Large-Scale Preparation of [13C]-Methyl Phenyl Sulfide from [13C]Methanol by a One-Step Process. Org. Process Res. Dev. 2002, 6, 851.

back to top

Related Links