ChemicalBook CAS DataBase List 3-AZIDO-3-DEOXY-1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE

3-AZIDO-3-DEOXY-1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE synthesis

9synthesis methods

Product Name:3-AZIDO-3-DEOXY-1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE
CAS Number:13964-23-3
Molecular formula:C11H17N3O6
Molecular Weight:287.27

α-D-Allofuranose, 1,2:5,6-bis-O-(1-methylethylidene)-, 3-(1,1,1-trifluoromethanesulfonate)

55951-90-1
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3-AZIDO-3-DEOXY-1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE

13964-23-3
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Yield:13964-23-3 99%

Reaction Conditions:

with sodium azide in N,N-dimethyl-formamide at 50; for 6 h;

Steps:

4 4.4 Synthesis of 1,2: 5,6-di-O-isopropylidene-3-azido-3-deoxy-α-D-allofuranose 5

NaN₃ (3.3 g, 0.05 mol) was added to a solution of compound 4 in 24.0 mL DMF. After stirring for 6 h at 50 °C, the reaction solution was diluted with CH₂Cl₂, washed with saturated NaHCO₃ and brine, dried over Na₂SO₄. The concentrate was purified by column chromatography (PE: EtOAc=12: 1) to give compound 5 (12.6 g, 99%).¹H NMR (CDCl_3, 400 MHz): δ 5.85 (d, J_1,2=3.6 Hz, 1H, H-1), 4.61 (d, J_1,2=3.6 Hz, 1H, H-2), 4.24 (m, 1H), 4.08-4.16 (m, 3H), 4.00 (dd, J_5,6a=4.8 Hz, J_5,6b=8.8 Hz, 1H, H-5), 1.51, 1.43, 1.37, 1.32 (4×s, 4×3H). ¹³C NMR (CDCl_3, 100 MHz): δ 112.2, 109.5, 110.3, 105.0, 80.4, 72.9, 67.6, 66.2, 26.8, 26.5, 26.3, 25.1. ESI-MS: calcd for C₁₂H₂₀N₃O₅ [M+H]⁺ 286.1325, found: 286.1380.