Diisopropylethylamine → (2S,3S)-3-(t-Butyldimethylsilyloxy)-2-methylhexanal

HRID 22075

Reaktionsgleichung

Reaktionsgleichung von HRID 22075
C[C@@]1(CO)[C@H](CCC)O1.[Si](OS(C(F)(F)F)(=O)=O)(C(C)(C)C)(C)C.CCN(C(C)C)C(C)C.[Si:34]([O:41][C@H:42]([CH2:47][CH2:48][CH3:49])[C@@H:43]([CH3:46])[CH:44]=[O:45])([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35]>>[Si:34]([O:41][C@@H:42]([CH2:47][CH2:48][CH3:49])[C@H:43]([CH3:46])[CH:44]=[O:45])([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:35])[CH3:36]

Komponenten

5

Edukt 4

HCID 81531DiisopropylethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 10931464(2R,3S)-2-Methyl-3-propyloxiranemethanolHCID 14959487(2R,3R)-3-[t-Butyldimethylsilyloxy)-2-methylhexanal

Produkt 1

HCID 10879364(2S,3S)-3-(t-Butyldimethylsilyloxy)-2-methylhexanal

Versuchsvorschrift

Epoxy alcohol 13, 1.25 eq TBSOTf, and 1.30 eq DIPEA were reacted as in the preparation of 16 to give the crude aldehyde 14 in 95% +yield. 1H NMR, 13C NMR, IR, and high resolution MS are identical to 16. [δ]D=+19.3° (c=1.10, CH2Cl2). 1H NMR integration of δ 9.67 and the contaminating diastereromer at δ 9.71 indicated a >50:1 ratio.

Quellen und Nachweise

ORD-Eintrag
ord-5cf56b8424ec43e3b8980dfd92998226
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05426206

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