Trimethylsilyl triflate → Isohexane ethyl acetate

The crude product compound [3] (0.27-7.14 g, 0.54-14.2 mmol) and 6-azidohexanol (0.27-3.54 g, 1.08-14.1 mmol) are dissolved in dry acetonitrile, at 0° C., molecular sieves (0.2-5 g, 3 Å) and trimethylsilyl trifluoromethanesulfonate (0.02-1.56 g, 0.1-7 mmol) are added. After the reaction is complete, the mixture is filtered and washed with saturated sodium bicarbonate solution. Concentration results in the crude product, which is purified by chromatography on silica gel with an ethyl acetate/isohexane gradient (0.17-2.23 g, 0.35-4.58 mmol, about 69% yield). The product is then taken up in methanol/hydrazine hydrate (1:1) 1-30 ml) and heated at 80° C. until reaction is complete. After evaporation of the solvent, the crude product is taken up in dichloromethane/methanol (1:1) and stirred at 0° C. with acetic anhydride (3.5-45.8 mmol) until reaction is complete. After evaporation, the azide is reduced with hydrogen in the presence of catalytic amounts of palladium on carbon (10%) (0.01-1.5 g) in methanol (0.5-40 ml). The crude product resulting after evaporation is purified by gel chromatography on Biogel P2 (compound [4];0.08-1.02 g, 0.25-3.2 mmol, about 70% yield). FAB-MS: M+H+ =321. 1H-NMR [300 MHz, DMSO]: 7.68 (HNAc), 4.23 (GlcNAc-H-1), 3.78-3.6 (m), 3.49-3.23 (m), 3.08-3.02 (m) 2.58, 179 (GlcNCOCH3), 1.51-1.21 (O--(CH2)--N).

1. filtrationthe mixture is filtered
2. washwashed with saturated sodium bicarbonate solution
3. concentrationConcentration
4. customresults in the crude product, which

ORD record

ord-0e48ace903844e45b3f51b131a75e4c5

Source dataset

uspto-grants-1995_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05470843