ChemicalBook CAS DataBase List 2-Azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside solution

2-Azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside solution synthesis

5synthesis methods

Product Name:2-Azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside solution
CAS Number:142072-11-5
Molecular formula:C16H24N4O9
Molecular Weight:416.3831

2-Chloroethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

887641-02-3
6 suppliers
inquiry

2-Azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside solution

142072-11-5
16 suppliers
$250.00/100mg

Yield:142072-11-5 80%

Reaction Conditions:

with sodium azide;tetra-(n-butyl)ammonium iodide in N,N-dimethyl-formamide at 80; for 15 h;

Steps:

4 4.4 2-Azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-d-glucopyranoside 16

Chloride 15 (1.36 g, 3.32 mmol) was dissolved in DMF (22 mL), and to this tetra-N-butylammonium iodide (1.29 g, 3.49 mmol) and sodium azide (863 mg, 13.3 mmol) were added. The reaction mixture was then heated to 80 °C and was then stirred at this temperature for 15 h. The reaction mixture was cooled, diluted with CH₂Cl₂ and washed with water. The aqueous layer was re-extracted with a portion of CH₂Cl₂. The organic portions were combined and were then washed with water. The organic layer was then washed with brine, dried over NaSO₄ and the solvent then removed. Chromatography (EtOAc/petroleum ether, 1:3 to 1:1 to 2:1 to 1:0) gave the title compound (1.10 g, 80%) as a white solid; ¹H NMR (500 MHz, CDCl₃-d) δ 5.50 (d, J=8.6 Hz, 1H, NH), 5.36 (dd, J=10.6, 9.3 Hz, 1H, H-3), 5.08 (dd, J=10.0, 9.3 Hz, 1H, H-4), 4.83 (d, J=8.3 Hz, 1H, H-1), 4.26 (dd, J=12.3, 4.7 Hz, 1H, H-6a), 4.15 (dd, J=12.3, 2.4 Hz, 1H, H-6b), 4.05 (ddd, J=10.8, 4.7, 3.2 Hz, 1H, OCH₂CH₂N₃), 3.80 (dt, J=10.7, 8.5 Hz, 1H, H-2), 3.74-3.66 (m, 2H, H-5, OCH₂CH₂N₃), 3.51 (ddd, J=13.5, 8.6, 3.3 Hz, 1H, OCH₂CH₂N₃), 3.26 (ddd, J=13.4, 4.7, 3.1 Hz, 1H, OCH₂CH₂N₃), 2.09 (s, 3H), 2.03 (s, 3H), 2.03 (s, 3H) (each OAc), 1.96 (s, 3H, NHAc); ¹³C NMR (126 MHz, CDCl₃): δ 170.74, 170.65, 170.40, 169.38 (each C=O), 100.46 (C-1), 72.04 (C-4), 71.97 (C-5), 68.55 (C-3), 68.41 (OCH₂CH₂N₃), 61.97 (C-6), 54.93 (C-2), 50.60 (OCH₂CH₂N₃), 23.37 (NHAc), 20.74, 20.66, 20.62 (each OAc); ES-HRMS calcd for C₁₆H₂₄N₄O₉Na 439.1441, found m/z 439.1429 [M+Na]⁺; IR (cm^-1): 2106, 1744, 1656, 1566, 1436, 1368, 1225, 1170, 1125, 1033, 910; R_f: 0.41 (1:19 MeOH/CH₂Cl₂); [α]_D²⁰ -22.8 (c 0.36, CHCl₃).