2-[N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)aMino]-2-deoxy-D-glucose synthesis
- Product Name:2-[N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)aMino]-2-deoxy-D-glucose
- CAS Number:174844-42-9
- Molecular formula:C12H14N4O8
- Molecular Weight:342.26
Yield:174844-42-9 75%
Reaction Conditions:
with sodium hydrogencarbonate in water;acetonitrile at 23; for 28 h;Darkness;Inert atmosphere;
Steps:
2-NBD-Glucosamine (3).[7]
Method A: To a solution of NBD-F 2 (48.7 mg, 0.266 mmol, 1.1 equiv) in 1 mL acetonitrile was added glucosamine HCl 8 (52.4 mg, 0.243 mmol, 1.0 equiv) and then 1 mL of a 0.3 M NaHCO3 solution (0.315 mmol, 1.2 equiv). The mixture was vigorously stirred to ensure that the aqueous and organic layers had mixed, and the reaction was allowed to stir for 28 h at 23 °C in the dark, producing a dark red/black solution. The reaction mixture was passed through a Celite plug and rinsed with MeOH. The resulting filtrate was concentrated in vacuo and loaded onto a silica column using the dry-loading technique (see above). Flash column chromatography of the residue on silica gel (solvent gradient: DCM, 19:1 DCM/MeOH, 9:1 DCM/MeOH, then 4:1 DCM/MeOH) afforded the desired product 3. Rf (17:3 CH3CN/H2O): 0.66. The film was redissolved in acetone, filtered through a Celite plug to remove the insoluble silica gel residue, and the solvent removed in vacuo to produce 3 as a red film (62 mg, 75%).
References:
Jung, Michael E.;Dong, Timothy A.;Cai, Xiaolu [Tetrahedron Letters,2011,vol. 52,# 20,p. 2533 - 2535] Location in patent:supporting information; experimental part
14131-63-6
6 suppliers
inquiry
10199-89-0
220 suppliers
$15.00/250mg
174844-42-9
13 suppliers
inquiry
29270-55-1
64 suppliers
$28.00/100mg
174844-42-9
13 suppliers
inquiry
1194-66-7
26 suppliers
$65.00/50mg
174844-42-9
13 suppliers
inquiry
29270-54-0
6 suppliers
inquiry
174844-42-9
13 suppliers
inquiry