3-O,5-O-Benzylidene-1-O,2-O-isopropylidene-α-D-glucofuranose synthesis

4synthesis methods

Product Name:3-O,5-O-Benzylidene-1-O,2-O-isopropylidene-α-D-glucofuranose
CAS Number:22164-09-6
Molecular formula:C16H20O6
Molecular Weight:308.3264

18549-40-1 Synthesis

18549-40-1
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3-O,5-O-Benzylidene-1-O,2-O-isopropylidene-α-D-glucofuranose

22164-09-6
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Yield:22164-09-6 56%

Reaction Conditions:

with benzaldehyde;Zinc chloride

Steps:

1 Synthesis of 3,5-O-benzylidene-1,2-O-isopropylidene-α-D-glucofuranoside

EXAMPLE 1 Synthesis of 3,5-O-benzylidene-1,2-O-isopropylidene-α-D-glucofuranoside To a mixture of 1,2-O-isopropylidene-α-D-glucofuranoside (3.0 g, 13.6 mmol) and anhydrous zinc chloride (4.0 g, 29.4 mmol) was added benzaldehyde (12.0 g, 114 mmol) at room temperature under nitrogen. The mixture was stirred for 4 hours, then diluted with ethyl acetate (EtOAc, 20 mL). The resulting solution was washed with water (2*40 mL), evaporated, and recrystallized from hexane at 0° C. to afford 3,5-O-benzylidene-1,2-O-isopropylidene-α-D-glucofuranoside (2.48 g, 56%) as a white solid. ¹H NMR (300 MHz, CDCl₃) δ7.47 (m, 2H), 7.36 (m, 3H), 6.03 (d, 1H, J=3.6 Hz), 5.84 (s, 1H), 4.65 (d, 1H, J=3.6 Hz), 4.46 (d, 1H, J=2.2 Hz), 4.36 (dd, 1H, J=7.1, 4.5 Hz), 4.11 (d, 1H, J=2.2 Hz), 4.06 (ddd, 1H, J=11.6, 7.1, 4.5 Hz), 3.91 (ddd, 1H, J=11.6, 7.1, 4.5 Hz), 1.86 (dd, 1H, J=7.1, 3.6 Hz), 1.51 (s, 3H), 1.32 (s, 3H); ¹³C NMR (75 MHz, CDCl₃) δ137.5 (C), 129.3 (CH), 128.3 (CH), 126.2 (CH), 111.9 (C), 104.9 (CH), 94.4 (CH), 83.8 (CH), 78.0 (CH), 74.0 (CH), 72.9 (CH), 61.9 (CH₂), 26.6 (CH₃), 26.0 (CH₃).

References:

US6294666,2001,B1