Reaction equation
[OH:1][C@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]>CN(C)C=O>[O:1]=[CH:2][C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[CH2:11]([OH:12])[C@H:9]1[O:10][C@H:2]([O:1][C@H:7]2[C@H:5]([OH:6])[C@@H:3]([OH:4])[C@H:2]([OH:1])[O:10][C@@H:9]2[CH2:11][OH:12])[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]1[OH:8].[CH2:11]([OH:12])[C@H:9]1[O:10][C@@H:2]([O:1][C@H:7]2[C@H:5]([OH:6])[C@@H:3]([OH:4])[C@H:2]([OH:1])[O:10][C@@H:9]2[CH2:11][OH:12])[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]1[OH:8].[OH:1][C@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]Participants
Procedure
AmB (800 mg, 0.86 mmol) was dissolved in 16 mL anhydrous dimethylformamide (DMF) and stirred for 5 min. α-D-Glucose (316 mg, 1.72 mmol) was added. The resulting solution was sealed to the atmosphere and placed in a water bath equilibrated to 37° C. for 6 hr. The reaction was followed by LCMS until judged complete. The reaction product was used directly in the amidation reaction, described infra, without purification. The corresponding D-galactose, D-maltose, D-cellobiose and α-D-galactose glycosylated rearrangement products were obtained using the same procedure, but substituting D-galactose (315 mg, 1.72 mmol), D-maltose hydrate (620 mg, 1.72 mmol), D-cellobiose (588 mg, 1.72 mmol) and α-D-lactose hydrate (620 mg, 1.72 mmol), respectively, for α-D-glucose.
Workup
- additionwas added
- customThe resulting solution was sealed to the atmosphere
- customThe reaction product was used directly in the amidation reaction
- customwithout purification
Sources & evidence
- ORD record
- ord-1d626a701b7f4211a44d2831ca34a338
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06664241B2
Linked notes
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