Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 863236Generated: October 30, 2026

Magnesium → 6(S)-Tert-butoxycarbonylamino-5(S)-hydroxy-3(R,S)-isopropyl-10-triisopropylsilyloxy-8,8-dimethyldec-1-ene

https://huagongshe.com/reaction/863236

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMagnesiumHCID 5462224—
Reactant(RS)-2-isopropyl-3-butenyl bromideHCID 10631133—
Reactant2(S)-Tert-butoxycarbonylamino-6-triisopropylsilyloxy-4,4-dimethyl-hexanalHCID 22882395—
Product6(S)-Tert-butoxycarbonylamino-5(S)-hydroxy-3(R,S)-isopropyl-10-triisopropylsilyloxy-8,8-dimethyldec-1-eneHCID 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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05719141
Source datasetuspto-grants-1998_02
ORD IDord-44ffebc66a794361b59a6e57bfd8da36
Source noteuspto-grants-1998_02