反应详情

3,4-Di-O-acetyl-1,2-dideoxy-6-O-tosyl-D-arabinohex-1-enopyranose (50g.) was dissolved in hexamethylphosphoramide (800 ml.) and sodium azide (34 g.) was added and the solution was stirred at 25° for 24 hours. The hexamethylphosphoramide was distilled off under high vacuum and the residue was taken up in chloroform and washed with water. The chloroform extract was dried (MgSO4), filtered and evaporated to give a crude gum which was chromatographed on a silica gel column (150 × 7.5 cm.) using 7% acetone in hexane as the eluent to give 3,4-di-O-acetyl-6-azido-1,2,6-trideoxy-D-arabinohex-1-enopyranose (25 g.) as a colorless gum, (Found: C, 47.23; H, 5.30; N, 16.37. C10N13N3O5 requires: C, 47.06; H, 5.13; N, 16.46%), [α]D26 × 25.1° (CH3OH), νmax (CHCl3) 2110, 1755, 1660, 1220, 1040 cm. -1, δ(CDCl3) 2.06, 2.09 (6H, s, OAc), 4.91 (1H, ddd, J = 6.5Hz, 3.0Hz, 1Hz, H2), and 6.53 ppm. (1H, dd, J = 6.5Hz, 1.5Hz, H1).

1. distillationThe hexamethylphosphoramide was distilled off under high vacuum
2. washwashed with water
3. extractionThe chloroform extract
4. dry with materialwas dried (MgSO4)
5. filtrationfiltered
6. customevaporated
7. customto give a crude gum which
8. customwas chromatographed on a silica gel column (150 × 7.5 cm.)