Document Type: Short communication

Authors

1 Indian Institute of Integrative Medicine, Canal Road, Jammu Tawi 180001, India

2 Department of Chemistry, Govt. Degree College (Boys) Baramulla, Jammu and Kashmir, India

3 Department of Chemistry, Govt. Degree College (Boys) Sopore, Jammu and Kashmir, India

10.33945/SAMI/CHEMM.2019.5.9

Abstract

The reactions of glycals with N-iodosuccinimide and acetic anhydride under solvent free conditions provide 2-deoxy-2-iodo-α-mannopyranosyl acetates with good stereoselectivity. The developed process is in accordance with principles of green chemistry and addresses the shortage of such methods for the regioselective iodo acetoxylation of alkenes.

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[16] General procedure (for model reaction): In a round bottom flask containing appropriate amount of styrene (0.12 mL) and acetic anhydride (3 mL) and the contents stirred for 5 min. followed by the addition of NIS (292.5 mg) at 0 °C. The reaction mixture is allowed to stir at 0 °C for 30 minutes under solvent free conditions. On completion of the reaction, the contents were diluted with water, the organic layer separated and the aqueous portion extracted with DCM (3×50 mL).  The combined organic layer was washed with water (2×10 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure at

[17] Spectral data for Iodoacetate 4l: 1H NMR (500 MHz, CDCl3), d 6.43 (s, 1 H), 5.36 (broad s, 1 H), 4.83 (apparent t, J = 4.2 Hz, 1 H), 4.34 (m, 1 H), 4.23 (dd, J = 4.2, 0.7 Hz, 1 H), 4.18 (d, J = 6.8 Hz, 2 H), 2.12 (s, 3 H), 2.08 (s, 3 H), 2.02 (s, 3 H), 1.98 (s, 3 H); 13C NMR (100 MHz, CDCl3), 171.69, 170.8, 169.3, 168.0, 93.8, 69.81, 66.67, 62.3, 20.8, 20.7, 20.5, 18.8; IR (thin film), 1749, 1434, 1372, 1218, 1133, 1073, 1051, 994, 939 cm-1.