Reaktion #520923

Reaktionsgleichung

(2S,3R,4R,5S)-2,5-bis-(N-(((benzyl)oxy)carbonyl)amino)-3,4-epoxy-1,6-diphenylhexane

sodium borohydride

trifluoroacetic acid

→

desired compound

Ausbeute 58.1%

(2S,3S,5S)-2,5-bis-(N-(((benzyl)oxy)carbonyl)amino)-1.6-diphenyl-3-hydroxyhexane

Ausbeute 58.1%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe resulting mixture was quenched with 1N aqueous HCl
2. 2
   workup.ADDITIONdiluted with water
3. 3
   workup.STIRRINGstirred for 16 h
4. 4
   FiltrationThe resulting mixture was filtered
5. 5
   Waschenwashed with water
6. 6
   Sonstigedried

Vorschrift

A mixture of 39.2 g (71.2 mmol) of (2S,3R,4R,5S)-2,5-bis-(N-(((benzyl)oxy)carbonyl)amino)-3,4-epoxy-1,6-diphenylhexane in 600 ml of THF was treated under N2 atmosphere with 13 g (0.36 mol) of sodium borohydride. The resulting mixture was treated dropwise with 27.7 ml (0.36 mol) of trifluoroacetic acid. After being stirred for 3.5 h at ambient temperature, the resulting mixture was quenched with 1N aqueous HCl, diluted with water, and stirred for 16 h. The resulting mixture was filtered, washed with water, and dried to provide 22.85 g (58%) of the desired compound as a white solid.

Quelle