ChemicalBook CAS DataBase List 1,2:3,4-Di-O-isopropylidene-D-galactopyranose

1,2:3,4-Di-O-isopropylidene-D-galactopyranose synthesis

8synthesis methods

Product Name:1,2:3,4-Di-O-isopropylidene-D-galactopyranose
CAS Number:4064-06-6
Molecular formula:C12H20O6
Molecular Weight:260.28

3646-73-9
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$403.00/5mg

67-64-1
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$17.30/10ml

1,2:3,4-Di-O-isopropylidene-D-galactopyranose

4064-06-6
209 suppliers
$11.00/1g

Yield:4064-06-6 75.6%

Reaction Conditions:

with sulfuric acid;zinc(II) chloride at 20; for 4 h;Inert atmosphere;

Steps:

2.3 Synthesis of 1,2;3,4-di-O-isopropylidene-D-galactose (IpGal) (2)
D-galactose (7g, 38.8mmol) and anhydrous ZnCl₂ (7.14g, 52.4mmol) were added to acetone (150mL) followed by H₂SO₄ (0.84mL) dropwise to the solution. It was allowed to react at room temperature for 4h under nitrogen atmosphere until the starting material completely disappeared. The solution was neutralized with saturated Na₂CO₃ solution after the reaction. After filtration, the solvent was removed under reduced pressure on a rotary evaporator. It was further extracted with diethyl etherand dried over anhydrous Na₂SO₄. The organic solvent was evaporated, and the product 2 was obtained as a pale-yellow viscous oil in 75.6% yield which was used for the next step without further purification. ¹H NMR (400MHz, CDCl₃) δ 5.57 (1H, d, J=5.2Hz, anomeric proton CH), 4.62 (1H, dd, J=8.0Hz, 2.4Hz, CH), 4.34 (1H, dd, J=5.2Hz, 2.4Hz, CH), 4.28 (1H, dd, J=8.0Hz, 1.7Hz, CH), 3.87-3.75 (3H, m, CH+CH₂), 2.14 (1H, m, OH), 1.45 (3H, s, CH₃), 1.33 (3H, s, CH₃), 1.25 (6H, s, 2CH₃); ¹³C NMR (100MHz, CDCl₃) δ 108.9, 96.5, 71.8, 71.0, 70.8, 68.4, 62.5, 26.2, 26.1, 25.1, 24.5; FTIR (ν ν (cm^-1) 3489 (br, O-H stretch), 2985, 2933 (C-H stretch), 1069 (C-O stretch).