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ChemicalBook CAS DataBase List 3-AZIDO-3-DEOXY-1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE
13964-23-3

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

9synthesis methods
-

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 (CDCl3, 400 MHz): δ 5.85 (d, J1,2=3.6 Hz, 1H, H-1), 4.61 (d, J1,2=3.6 Hz, 1H, H-2), 4.24 (m, 1H), 4.08-4.16 (m, 3H), 4.00 (dd, J5,6a=4.8 Hz, J5,6b=8.8 Hz, 1H, H-5), 1.51, 1.43, 1.37, 1.32 (4×s, 4×3H). 13C NMR (CDCl3, 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.

References:

Wang, A-Peng;Liu, Chao;Yang, Shuang;Zhao, Zhehui;Lei, Pingsheng [Tetrahedron,2016,vol. 72,# 2,p. 285 - 297]

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