2-N-CARBOBENZYLOXY-2-DEOXY-D-GLUCOSAMINE synthesis
- Product Name:2-N-CARBOBENZYLOXY-2-DEOXY-D-GLUCOSAMINE
- CAS Number:16684-31-4
- Molecular formula:C14H19NO7
- Molecular Weight:313.3
Yield:16684-31-4 74%
Reaction Conditions:
with amberlite (OH(1-)) resin in water at 0 - 20; for 16 h;
Steps:
24.1
Example 24: Preparation of methyl 2-benzyloxycarbonylamino-2-deoxy-3-O-[4-methoxyphenyl(ethoxy-L-alanyl)]phosphoramidate-D-glucopyranoside (compound 26); 1. Preparation of N-benzyloxycarbonyl-D-glucosamine; To a stirring solution of benzyl chloroformate (5.5 mL, 6.7 g, 39.1 mmol) and amberlite (OH-) resin (1.4 mmol/ ml eq), (41 mL, 57.5 mmol) in water (50 mL) at 0°C, glucosamine HCl (5.0 g, 23.0 mmol), was added.The reaction was warmed to room temperature whilst stirring and monitored by TLC (dichloromethane/methanol 8/2 V/V). After 16 h the reaction was completed, the solution was filtered to remove the resin, then evaporated under reduced pressure and vacuum gun to give a white solid (5.3g, 17.0 mmol, 74%). 1H-NMR ((CD3)2SO, 500 MHz), mixture of α and β anomers (ratio 2.4: 1.0): δ 7.49- 7.41 (5H, m), 5.20 (1H, app. s), 4.99 (2H, s), 4.95 (1H, app. s), 4.65 (bs), 4.45 (bs), 3.57- 3.00 (6H, m), 3.30 (bs), 2.59 (bs), 2.50 (bs); 13C-NMR (DMSO, 125 MHz): δ 156.08, 137.08, 128.30, 127.72, 95.43, 90.66, 71.98, 70.97, 70.26, 65.22, 65.02, 61.17, 61.07, 56.35
References:
EP2471802,2012,A1 Location in patent:Page/Page column 24-25
111239-66-8
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16684-31-4
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57-48-7
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![D-Glucose, 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-, 1-(diethyl dithioacetal) (9CI)](/CAS/20210305/GIF/91625-01-3.gif)
91625-01-3
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16684-31-4
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