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1-Naphthyl-2.3.4.6-tetra-O-acetyl-β-D-glucopyranosid, Hydrolyse in MeOH;
entspr. Benzylether, H2, Pd-C;
4
[ 19939-82-3 ]
1-naphthyl β-D-glucopyranoside-6-sulfate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
45%
With sulfur trioxide pyridine complex In N,N-dimethyl-formamide at -20 - 20℃; for 12h;
4.1.2. Methyl α-D-glucopyranoside-6-sulfate (5b)
General procedure: To a solution of methyl α-D-glucopyranoside (0.58 g, 3.0 mmol)in anhydrous DMF (9 mL) at -20 °C, was added a solution of SO3.pyridine (0.50 g, 3.15 mmol) in 1 mL anhydrous DMF, The resulting solution was stirred at r.t. for 12 h and concentrated invacuo, giving a residue that was subjected to silica gel chromatographto give 0.435 g (50%) of 5b.
With Aloe*arborescens*glycosyltransferase*GT3 In dimethyl sulfoxide at 30℃; for 12h; Enzymatic reaction;
Preparative scale reactions
General procedure: Generally 30-50 μmol of aglycon was solved in 0.5 mL DMSO and diluted with buffer solution (50 mM Tris HCl, pH 7.4, 25 mL total volume). UDP-Glc (60100 μmol) was added along with 50 mL of crude enzyme of AaGT3, extracted from 3 g in wet induced E. coli cells with pET28a-AaGT3. The reactions were performed at 30 °C for up to 12 h, followed by adding 5 × 100 mL of ethyl acetate to extract 5 times. The organic phase was evaporated to dryness under reduced pressure, and the residue was dissolved in 1.5 mL of methanol and purified by reverse-phase semi-preparative HPLC. The obtained products were analyzed by MS and NMR.