Sodium Azide → 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxyhexopyranose

HRID 1637435Notes

Reaction equation

[C:1]([O:4][C@@H:5]1[O:26][C@H:25]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@@H:6]1OS(C(F)(F)F)(=O)=O)(=[O:3])[CH3:2].[N-:32]=[N+:33]=[N-:34].[Na+]>CN(C=O)C.C(Cl)Cl>[N:32]([C@@H:6]1[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@@H:25]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[O:26][C@H:5]1[O:4][C:1](=[O:3])[CH3:2])=[N+:33]=[N-:34]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of mannose triflate 56 (1.28 g, 2.66 mmol) in 14 mL of DMF is added sodium azide (0.69 g, 10.5 mmol). The reaction mixture is heated at 40° C. for 1.75 h, cooled to room temperature, diluted with 100 mL of CH2Cl2, washed with H2O (100 mL), saturated NaCl (100 mL), dried over MgSO4, filtered, and concentrated to afford a yellow oil. The product is purified by flash chromatography (33% EtOAc/hexane) to afford 0.80 g (81%) of 2-azido-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucopyranose 57: Rf 0.31 (33% EtOAc/hexane) δ 5.55 (d, J=8.6 Hz, 1H, H-1), 5.015.15 (m, 2H, H-3, H-4), 4.31 (dd, J=12.7, 4.5 Hz, 1H, H-6), 4.08 (d, J=12.5 Hz, 1H, H-6), 3.77-3.84 (m, 1H, H-5), 3.69 (app t, J=9.1 Hz, 1H, H-2), 2.10 (s, 3H), 2.08 (s, 3H), 2.05 (s, 3H), 2.03 (s, 3H).

Workup

temperaturecooled to room temperature
washwashed with H2O (100 mL), saturated NaCl (100 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customto afford a yellow oil
customThe product is purified by flash chromatography (33% EtOAc/hexane)

Sources & evidence

ORD record: ord-1ad221b3074f48ea82869e35b565bb40
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06040433

Reaction notes

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