反応 #87465

反応方程式

1-bromomethyl-4-methoxy-benzene

((3S,4S,5R)-6-allyloxy-3,4,5-tris-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-2-yl)-methanol

Sodium hydride

→

product

収率 52.0%

(3S,4S,5R)-6-allyloxy-3,4,5-tris-benzyloxy-2,2-bis-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran

収率 52.0%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   温度The reaction was then heated to 60° C. overnight
2. 2
   温度The mixture was cooled down to room temperature
3. 3
   その他the reaction was quenched with water
4. 4
   抽出extracted with ethyl acetate (2 times)
5. 5
   洗浄The combined organic layers were washed with water, brine
6. 6
   乾燥dried over sodium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated under reduced pressure
9. 9
   その他The reaction was then chromatographed over silica gel (
10. 10
    洗浄eluting with a gradient of 0 to 80% ethyl acetate in heptane)

実験手順

The starting diol [((3S,4S,5R)-6-allyloxy-3,4,5-tris-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-2-yl)-methanol (I-1b: 10 g, 19.208 mmol) was dissolved in N,N-dimethylformamide (70 mL) and cooled to 0° C. Sodium hydride (60% dispersion in mineral oil, 1.69 g, 42.3 mmol) was added and the reaction was allowed to stir at 0° C. for 1 hour before the addition of 1-bromomethyl-4-methoxy-benzene (5.96 mL, 40.3 mmol). The reaction was then heated to 60° C. overnight. The mixture was cooled down to room temperature and the reaction was quenched with water and extracted with ethyl acetate (2 times). The combined organic layers were washed with water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The reaction was then chromatographed over silica gel (eluting with a gradient of 0 to 80% ethyl acetate in heptane) yielding 7.55 g (52% yield) of product (I-1c). MS 778.8 (M+NH4+; positive mode).

出典