3,4-dihydro-2H-pyran → benzyl (2S,3S,5R)-2-hexyl-3-[(t-butyldimethylsilyl)oxy]-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate

HRID 1681975

Reaktionsgleichung

[CH2:1]([C@@H:7]([C@@H:18]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH2:19][C@H:20]([OH:32])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[O:41]1[CH:46]=[CH:45][CH2:44][CH2:43][CH2:42]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH2:1]([C@@H:7]([C@@H:18]([O:33][Si:34]([C:37]([CH3:38])([CH3:39])[CH3:40])([CH3:36])[CH3:35])[CH2:19][C@H:20]([O:32][CH:42]1[CH2:43][CH2:44][CH2:45][CH2:46][O:41]1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

Reaktionsbedingungen

Temperatur: -15 °C

Versuchsvorschrift

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).

Aufarbeitung

customThereupon, the solution was evaporated
customthe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-b4cc2c6c7bd54aefae625584e9d8470f
Quelldatensatz: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05175186

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