Diethyl Ether → HCID 22808782, compound

Participants

Reaction Steps

4-O-Acetyl-3-deoxy-6-O-tosyl-D-glucal (550 mg.) and sodium azide (550 mg.) were dissolved in hexamethylphosphoramide (50 ml.) and the mixture was stirred at 25° for 24 hours. The reaction mixture was poured into ether and extracted with water and the ether extract was dried (MgSO4) and evaporated and the product was chromatographed on a silica gel column (58 × 2.5 cm) using 7% acetone in hexane as the eluent to give 4-O-acetyl-6-azido-3,6-dideoxy-D-glucal (200 mg.) as a colorless oil, (Found: C, 48.84; H, 5.33; N,21.49. C8H11N3O3 requires: C, 48.72; H, 5.62; N, 21.31%), [α]D26 = 158.8° (CH3OH), νmax (film) 2100, 1720, 1660, 1220, 1050 cm.-1, δ(CDCl3) 2.09 (3H, s, OAc), 4.72 (1H, ddd, H = 6Hz, J = 4.5Hz, J = 3Hz, H2) and 6.39 ppm (1H, ddd, J = 2Hz, J = H1. )

Provenance & Evidence