Bi[5,5-bis(hydroxymethyl)-3-methyl-2-oxomorpholin-3-yl] (BHM-3 dimer). A low toxicity, water-soluble, one-electron reducing agent

@article{Gaudiano1993Bi55bishydroxymethyl3methyl2oxomo,
  title={Bi[5,5-bis(hydroxymethyl)-3-methyl-2-oxomorpholin-3-yl] (BHM-3 dimer). A low toxicity, water-soluble, one-electron reducing agent},
  author={Giorgio Gaudiano and Elizabeth L. Frank and Michael S. Wysor and Steven D. Averbuch and Tad H. Koch},
  journal={Journal of Organic Chemistry},
  year={1993},
  volume={58},
  pages={7355-7363}
}
Bi[5,5-bis(hydroxymethyl)-3-methyl-2-oxomorpholin-3-yl] (BHM-3 dimer) was synthesized by condensing tris(hydroxymethyl)aminomethane with ethyl pyruvate to form 5,6-dihydro-5,5-bis(hydroxymethyl)-3-methyl- 1,4-oxazin-2-one (1) followed by photoreduction in 2-propanol. BHM-3 dimer exists in equilibrium with 5,5-bis(hydroxymethyl)-3-methyl-2-oxo- morpholin-3-yl (BHM-3) in solution; the rate constant for BHM-3 formation from dimers varies with solvent increasing from 5.3×10 -6 s -1 in acetonitrile… 
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Polycyclic compounds from aminopolyols and alpha-dicarbonyls: structure and application in the synthesis of exoditopic ligands.

TLDR
The structure and stereochemistry of the crystalline 2 : 2 condensation product ("glytham") of glyoxal and tris(hydroxymethyl)aminomethane was conclusively determined by X-ray diffractometric analysis and suggests the employment of glytham as starting material for the synthesis of ditopic ligands for metal ions.

Photoinduced Formation of β-Oxy-α,α-disubstituted-α-amino Acid Derivatives from Ketoximes

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