HuagongsheHuagongshe Chemistry Print Report · For research reference only
Magnesium → 6(S)-Tert-butoxycarbonylamino-5(S)-hydroxy-3(R,S)-isopropyl-10-triisopropylsilyloxy-8,8-dimethyldec-1-ene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Magnesium | HCID 5462224 | — |
| Reactant | (RS)-2-isopropyl-3-butenyl bromide | HCID 10631133 | — |
| Reactant | 2(S)-Tert-butoxycarbonylamino-6-triisopropylsilyloxy-4,4-dimethyl-hexanal | HCID 22882395 | — |
| Product | 6(S)-Tert-butoxycarbonylamino-5(S)-hydroxy-3(R,S)-isopropyl-10-triisopropylsilyloxy-8,8-dimethyldec-1-ene | HCID 22882581 | — |
Reaction Steps
The title compound is prepared in a manner analogous to that described in Example 35f) starting from 23.9 g of 1-bromo-2(R,S)-isopropyl-3-butene (preparation according to D. Mesnard et al., C.R. Acad. Sci. Paris, t. 277, Series C-567), 3.3 g of magnesium powder and 11.25 g of 2(S)-tert-butoxycarbonylamino-6-triisopropylsilyloxy-4,4-dimethyl-hexanal (Example 1g). The crude product is purified by FC over 900 g of silica gel (mobile phase E) to give the title compound as a diastereomer mixture: Rf (E)=0.31.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05719141 |
| Source dataset | uspto-grants-1998_02 |
| ORD ID | ord-44ffebc66a794361b59a6e57bfd8da36 |
| Source note | uspto-grants-1998_02 |