2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl azide → (2R,3R,4S,5S,6R)-2-(Acetoxymethyl)-6-aminotetrahydro-2H-pyran-3,4,5-triyl triacetate
Reaction equation
[C:1]([O:4][C@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1[N:24]=[N+]=[N-])(=[O:3])[CH3:2].[H][H]>[Ni].C(OCC)(=O)C>[C:1]([O:4][C@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[NH2:24])(=[O:3])[CH3:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a mixture of about 3.0 grams of 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl azide, 0.5 grams Raney nickel catalyst, and 40 ml. ethyl acetate, is vigorously agitated with hydrogen at atmospheric pressure, at a temperature of about 25° C. for a period of about 6.5 hours. The reaction mixture is filtered through diatomaceous silica, and the filtered solution is evaporated in vacuo to a syrup which crystallizes upon standing at a temperature of about 5° C. The crystalline product is recrystallized from 2-propanol to give about 1.7 grams of 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosylamine; m.p. 145°-147° C.; [α]D25 -9.8° (c 1.02, methanol).
Workup
- filtrationThe reaction mixture is filtered through diatomaceous silica
- customthe filtered solution is evaporated in vacuo to a syrup which
- customcrystallizes
- customupon standing at a temperature of about 5° C
- customThe crystalline product is recrystallized from 2-propanol
Sources & evidence
- ORD record
- ord-954705fc64c94f02bc1a10d0eb0609ee
- Source dataset
- uspto-grants-1980_10
- Patent number
- US04228274
Reaction notes
Loading…