Dimethylformamide → Fucose n-Decyl Acrylamide
Reaction equation
C(N([CH2:6][CH3:7])CC)C.[O:8]=[CH:9][C@H:10]([C@@H:12]([C@@H:14]([C@H:16]([CH3:18])[OH:17])[OH:15])[OH:13])[OH:11].[CH2:19](N)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C[N:31](C)[CH:32]=[O:33]>>[O:8]=[CH:9][C@H:10]([C@@H:12]([C@@H:14]([C@H:16]([CH3:18])[OH:17])[OH:15])[OH:13])[OH:11].[CH2:19]([C:6](=[CH2:7])[C:32]([NH2:31])=[O:33])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]Participants
5
Procedure
To a solution of pNAS (1.0 g, 5.91 mmol) in dimethylformamide (DMF, 50 mL) was added triethylamine (1.0 L), followed by the dropwise addition of the L-fucose derivative 22 (356 mg, 1.18 mmol, 20 mol % with respect to PNAS). The solution was stirred at room temperature for 16 h, and subsequently heated to 40° C. for 18 h. The solution was cooled and n-decylamine (233 mg, 25 mol % with respect to pNAS) was added as a solution in DMF (1 mL). The clear solution was stirred at room temperature for 12 h, followed by dialysis against water using dialysis tubing with a cut-off of 12,000-14,000 kD. The product was recovered by lyophilization. Yield 74%.
Workup
- temperaturesubsequently heated to 40° C. for 18 h
- temperatureThe solution was cooled
- stirringThe clear solution was stirred at room temperature for 12 h
- customfollowed by dialysis against water using dialysis tubing with a cut-off of 12,000-14,000 kD
- customThe product was recovered by lyophilization
Sources & evidence
- ORD record
- ord-a7b49286f27143a9b0a3cecc66624728
- Source dataset
- uspto-grants-1999_04
- Patent number
- US05891862
Reaction notes
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