(3R,4S)-4,5-ISOPROPYLIDENE PENT-2-EN-3-OL synthesis

9synthesis methods

Product Name:(3R,4S)-4,5-ISOPROPYLIDENE PENT-2-EN-3-OL
CAS Number:18524-19-1
Molecular formula:C8H14O3
Molecular Weight:158.2

D-erythro-Pent-1-enitol, 1,2-dideoxy-3-O-[(1,1-dimethylethyl)diphenylsilyl]-4,5-O-(1-methylethylidene)-

223558-55-2
0 suppliers
inquiry

(3R,4S)-4,5-ISOPROPYLIDENE PENT-2-EN-3-OL

18524-19-1
10 suppliers
inquiry

Yield:18524-19-1 96%

Reaction Conditions:

with tetrabutyl ammonium fluoride in tetrahydrofuran at 0 - 20; for 24 h;

Steps:

Deprotection of silyl ethers

General procedure: To a stirred and cooled to 0 °C solution of silyl ether 21 or 22 (3.96 g, 10 mmol) in THF (100 mL),TBAF3H2O (3.8 g, 1.2 equiv) was added. The cooling bath was removed, the mixture was stirred atroom temperature for 24 h, and concentrated to ca. 20 mL, water (50 mL). Methylene dichloride (50mL) was added. The layers were separated and the aqueous one extracted with DCM (2 × 30 mL).Combined organic solutions were dried, concentrated, and the residue was purified bychromatography (100% hexanes to 100% AcOEt) to yield 19 or 23 as colorless oil.

References:

Malik, Micha?;Jarosz, S?awomir [Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 2602 - 2608] Location in patent:supporting information