HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (2S,3S)-3-(t-Butyldimethylsilyloxy)-2-methylhexanal
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | tert-Butyldimethylsilyl trifluoromethanesulphonate | HCID 123564 | — |
| Reactant | (2R,3S)-2-Methyl-3-propyloxiranemethanol | HCID 10931464 | — |
| Reactant | (2R,3R)-3-[t-Butyldimethylsilyloxy)-2-methylhexanal | HCID 14959487 | — |
| Product | (2S,3S)-3-(t-Butyldimethylsilyloxy)-2-methylhexanal | HCID 10879364 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05426206 |
| Source dataset | uspto-grants-1995_06 |
| ORD ID | ord-5cf56b8424ec43e3b8980dfd92998226 |
| Source note | uspto-grants-1995_06 |