Potassium borohydride → (-)-2,3-O-Isopropylidene-D-threitol
反応式
[CH3:1][C:2]1([CH3:15])[O:6][C@H:5]([C@H:7]([OH:10])CO)[C@@H:4]([C@H:11]([OH:14])CO)[O:3]1.I([O-])(=O)(=O)=O.[Na+].[BH4-].[K+]>>[CH3:1][C:2]1([CH3:15])[O:3][C@H:4]([CH2:11][OH:14])[C@@H:5]([CH2:7][OH:10])[O:6]1参加物
実験手順
The starting material (1) (3,4-O-isopropylidene-D-mannitol) was reacted with sodium periodate and potassium borohydride as described in J. Chem. Soc., Perkin Trans. I., 1972, 275 (the contents of which are herein incorporated by reference) to yield compound (2) in 92% yield. Compound (2) (5.1 g) was dissolved in pyridine (40 ml) and cooled in ice. To this solution was added methanesulphonyl chloride (18 ml), dropwise with stirring. The mixture was allowed to stand at room temperature for 3 hours, after which time it was added to a solution of sodium bicarbonate. This solution was then extracted with dichloromethane (5×50 ml) and the combined extracts were dried (MgSO4) and concentrated in vacuo. The residue obtained was recrystallised from ethanol to give 2,3-O-isopropylidene-1,4-di-O-methanesulphonyl-D-threitol (3), (6.6 g, 66%), m.p. 83°-85° C.
出典と根拠
- ORDレコード
- ord-6388f129602f42c5ac21d93b34aa013e
- 出典データセット
- uspto-grants-1988_11
- 特許番号
- US04783452
反応ノート
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