2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-b-D-galactopyranose synthesis
- Product Name:2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-b-D-galactopyranose
- CAS Number:3006-60-8
- Molecular formula:C16H23NO10
- Molecular Weight:389.35
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Yield:3006-60-8 94%
Reaction Conditions:
with pyridine at 0;Inert atmosphere;
Steps:
1 Preparation of D-galactosamine pentaacetate (NAG2)
D-Galactosamine (25.0 g, 116 mmol) was suspended in anhydrous pyridine (250 mL) and cooled to 0 00 under an inert atmosphere. Acetic anhydride (120 mL, 1160 mmol) was added over the course of 2 h. After stirring overnight, the reaction mixture was concentrated in vacuo. Upon addition of methanol, a white solid precipitated and wascollected via filtration to provide the desired product (42.1 g, 93% yield). 1H NMR (ODd3, 500 MHz): O5.69 (d, 1H, J9.0 Hz), 5.40 (m, 1H), 5.37 (d, 1H, J3.0 Hz), 5.08 (dd, 1H, J3.0 Hz, 11 Hz), 4.44(dt, 1H, J9.5 Hz, 11 Hz), 4.17 (dd, 1H, J7.0 Hz, 11.5 Hz), 4.11 (dd, 1H, , J7.0 Hz, 11.5 Hz), 4.01 (t, 1H, J7.0 Hz),2.17 (s, 3H), 2.13 (s, 3H), 2.05 (s, 3H), 2.02 (s, 3H), 1.94 (s, 3H), 1.57 (s, 3H).
References:
WO2017/100461,2017,A1 Location in patent:Page/Page column 60
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