Opening of thiiranes: preparation of orthogonal protected 2-thioglyceraldehyde.
Treatment of acrolein diethyl acetal sulfide 8 with methanesulfenyl bromide at low temperature results in an efficient thiirane ring opening to a halo disulfide 9. The bromine in this halo disulfide is easily substituted by silver acetate, sodium azide, sodium iodide, and silver nitrate. Treatment of 9 with tetrabutylammonium acetate yields a novel dehydrohalogenation product 12. Silica gel converts bromide 9 into a disulfide-substituted version of acrolein 15. The orthogonal-protected version of 2-thioglyceraldehyde 13 can be deprotected to a useful form of this aldehyde.
Silvestri
M G
MG
Department of Chemistry and Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Wong
C H
CH
D005985:Glyceraldehyde / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013440:Sulfides / Q000737:chemistry*
D013440:Sulfides; D005985:Glyceraldehyde; C013523:ethylene sulfide