Reaktion #1769157

Reaktionsgleichung

benzyl (2S,3S,5R)-2-hexyl-3-[(t-butyldimethylsilyl)oxy]-5-hydroxyhexadecanoate

3,4-dihydro-2H-pyran

p-toluenesulfonic acid monohydrate

→

benzyl (2S,3S,5R)-2-hexyl-3-[(t-butyldimethylsilyl)oxy]5-[(tetrahydro-2 H-pyran-2-yl)oxy]hexadecanoate

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThereupon, the solution was evaporated
2. 2
   Sonstigethe residue was chromatographed on silica gel

Vorschrift

M)f) 350 mg of benzyl (2S,3S,5R)-2-hexyl-3-[(t-butyldimethylsilyl)oxy]-5-hydroxyhexadecanoate and 0.5 ml of freshly distilled 3,4-dihydro-2H-pyran were dissolved in 10 ml of methylene chloride and cooled to -15° C. A crystal of p-toluenesulfonic acid monohydrate was added thereto. The mixture was stirred until the reaction has finished. Thereupon, the solution was evaporated and the residue was chromatographed on silica gel. There were obtained 330 mg of benzyl (2S,3S,5R)-2-hexyl-3-[(t-butyldimethylsilyl)oxy]5-[(tetrahydro-2 H-pyran-2-yl)oxy]hexadecanoate, MS: 603 (M+ -t-butyl).

Quelle