1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxyhexopyranose → HCID 21967595, compound
Reaction equation
[N:1]([C@@H:4]1[C@@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:12]([O:18][C:19](=[O:21])[CH3:20])[C@@H:11]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[O:10][C@H:5]1OC(=O)C)=[N+:2]=[N-:3].[OH:27][C:28]1[CH:33]=[CH:32][C:31]([SH:34])=[CH:30][CH:29]=1>C(Cl)Cl>[N:1]([C@@H:4]1[C@@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:12]([O:18][C:19](=[O:21])[CH3:20])[C@@H:11]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[O:10][CH:5]1[S:34][C:31]1[CH:32]=[CH:33][C:28]([OH:27])=[CH:29][CH:30]=1)=[N+:2]=[N-:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
To a solution of 2-azido glucose tetraacetate 57 (0.222 g, 0.59 mmol) in 6.6 mL of CH2Cl2 is added 4-hydroxythiophenol (0.146 g, 1.15 mmol) followed by boron trifluoride diethyl ether complex (15.9 mL, 18.4 g. 141 mmol). The reaction mixture is heated at 45° C. for 12 h and then quenched by the addition of 2 mL of H2O. The reaction mixture is diluted with 25 mL of CH2Cl2, washed with H2O (10 mL), saturated NaCl (10 mL), dried over Na2SO4, filtered, and concentrated to afford 0.232 g of crude 2-azido-1,2-dideoxy-1-(4-hydroxyphenylthio)-3,4,6-tri-O-acetyl-α,β-D-glucopyranose 58 as a yellow oil, a mixture of anomers which is then taken on to the next step without further purification.
Workup
- customquenched by the addition of 2 mL of H2O
- additionThe reaction mixture is diluted with 25 mL of CH2Cl2
- washwashed with H2O (10 mL), saturated NaCl (10 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c20c9c451ad54684b07ac69824170e80
- Source dataset
- uspto-grants-2000_03
- Patent number
- US06040433
Reaction notes
Loading…