Sodium Azide → HCID 10872412, compound

Participants

Reaction Steps

The acceptor, ethyl 2-azido-2-deoxy-D-glucopyranoside was prepared as follows: Triacetyl-D-glucal was azidonitrated [Lemieux et al., Can. J. Chem., 57:1244 (1979)][NaN3 and Ce(NH4)2(NO3)6 in CH3CN] and acetolyzed (NaOAc in AcOH) to give 2-azido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucopyranose, which was treated with TiBr4 in CH2Cl2 and EtOAc, giving a glycosyl bromide, then glycosylated with EtOH in the presence of AgOTf and MS 4 Å in CH2Cl2 to give after O-deacetylation with NaOMe in MeOH, ethyl 2-azido-2-deoxy-D-glucopyranoside (22 percent overall yield) as a mixture of α and β 1:1.5. 1H NMR (D2O) δ: 1.21 (t, J 7.80 Hz, OCH2CH3 of β anomer), 1.22 (t, J 7.80 Hz, OCH2CH3), 2.99 (dd, J 7.43, 9.83 Hz, H-2 of β anomer), 5.11 (d, J 3.58 Hz, H-1 of a anomer). HRMS calcd for C8H15N3O5Cs (M+Cs+) 366.0066, found 366.0066.

Provenance & Evidence