HCID 2725013, compound → Ninhydrin

2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl azide (1.56 g, 4.18 mmol.) was dissolved in ethanol (50 ml). The resulting solution was subjected to catalytic hydrogenation in the presence of Raney nickel T-4 catalyst (1.5 ml) under the initial hydrogen pressure of 50 psi for 24 hours to reduce the azide group into amino group. From the reaction solution was taken out a portion thereof which was subjected to TLC on silica gel developed with a developer system of benzene-acetone (9:1 by volume). According to this TLC analysis, the completion of the reaction was confirmed by detecting whether the reduction product gave a ninhydrin-positive single spot of Rf 0.18. After this, the reaction solution was filtered to remove the catalyst, and the filtrate was concentrated under reduced pressure, affording the O-acetylglucosylamino compound as the white crystalline residue. This residue was taken up into dioxane (10 ml), and to the resultant solution were added N-carbobenzoxy-glycine N-hydroxy-succinimide active ester (1.27 g, 1.05 moles per mole of the starting compound) and triethylamine (0.58 ml, 1 mole per mole of the starting compound). The mixture was held at room temperature for 6 hours to effect the reaction for formation of the condensation product.

ORD record

ord-c6f730f74f44493891575cde149a0c3e

Source dataset

uspto-grants-1984_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04472379