Reaction equation
C(N)C1C=CC=CC=1.C([O:12][CH:13]1[S:30][CH2:29][C@@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:14]1[O:15][C:16](=[O:18])[CH3:17])(=O)C>CCOCC>[C:16]([O:15][C@@H:14]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:24]([O:25][C:26](=[O:28])[CH3:27])[CH2:29][S:30][C@@H:13]1[OH:12])(=[O:18])[CH3:17]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
22 ml (0.2 mol) of benzylamine are added under an inert atmosphere to a solution of 15 g (44.8.10-3 mol) of 1,2,3,4-tetra-O-acetyl-5-thio-D-xylopyranose in 450 ml of ether. After 7 hours at room temperature (15°-25° C.), the reaction mixture is concentrated under reduced pressure and the residue is dissolved in methylene chloride and washed with a 1N solution of hydrochloric acid, a saturated solution of ammonium chloride and then water. The solution obtained is dried over sodium sulfate and the solvent is evaporated off under reduced pressure. 6.2 g (yield: 47%) of the expected product are obtained after purification by chromatography on silica gel using a hexane/ethyl acetate mixture (3/2 v/v) as the eluent, and crystallization from an ethyl acetate/hexane mixture, said product having the following physical characteristics:
Workup
- concentrationthe reaction mixture is concentrated under reduced pressure
- dissolutionthe residue is dissolved in methylene chloride
- washwashed with a 1N solution of hydrochloric acid
- customThe solution obtained
- dry with materialis dried over sodium sulfate
- customthe solvent is evaporated off under reduced pressure
Sources & evidence
- ORD record
- ord-e496953e1a8048e29a65351a07d1384b
- Source dataset
- uspto-grants-1993_09
- Patent number
- US05246961
Linked notes
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