Reaktion #937703

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 1 N 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 1 N 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