Реакция #49652

Уравнение реакции

Me2S

Ozone oxygen

(3S,4S)-N-[(tert-Butyloxy)carbonyl]-4-amino-3-acetoxy-5-phenylpentene

Oxygen

→

title compound

(2R, 3S)-N-[(tert-Butyloxy)carbonyl]-3-amino-2-acetoxy-4-phenylbutanal

Растворители

methylene chloride

Условия реакции

Обработка

1. 1
   Другоеprepared by the method of Hanson et al., J
2. 2
   Температураto warm to 0°-5° C.
3. 3
   ДругоеThe solvent was removed at 0° C. under vacuum

Методика

Ozone/oxygen was bubbled at -70° C. into a solution of (3S,4S)-N-[(tert-Butyloxy)carbonyl]-4-amino-3-acetoxy-5-phenylpentene (2.55g, 8.0 mmol) [prepared by the method of Hanson et al., J. Ora. Chem., 50, 5399 (1985)] in 100 mL of methylene chloride until a deep blue color persisted. Oxygen was introduced until the blue color completely faded, then 3.0 mL of Me2S was added and the solution was allowed to warm to 0°-5° C. and stand overnight. The solvent was removed at 0° C. under vacuum yielding the title compound as a thick yellow oil which was used without further purification.

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