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HRID1952285

反应详情

EQUATION

反应方程式

HRID 1952285 的结构方程式

REACTANTS

反应物

1
结构：CC(=O)OC[C@@H]1C[C@@H](O[Si](C)(C)C(C)(C)C)CC(=O)O1
HCID16113281

未命名化合物

PRODUCTS

生成物

1
结构：CC(C)(C)[Si](C)(C)O[C@H]1CC(=O)O[C@H](CO)C1
HCID10659025

未命名化合物

收率 30%

AUXILIARIES

试剂、催化剂与溶剂

3
结构：[Sn]
催化剂HCID5352426

Tin atom

Sn

结构：CO
溶剂HCID887

Methanol

CH4O

结构：C1CCOC1
溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

((2S,4R)-4-(tert-butyldimethylsilyloxy)-6-oxotetrahydro-2H-pyran-2-yl)methyl acetate (VI) (0.625 g, 80% purity, 1.65 mmol) was dissolved in THF (8 mL) and MeOH (8 mL). Tin catalyst (tBu2SnClOH)2 (94 mg, 0.1 eq) was added and the reaction was stirred overnight. Reaction was concentrated and purified by flash chromatography to give pure (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one (VII) (126 mg, 30%). VII was found to contain less than 0.1% of enantiomer.

WORKUP

后处理

  1. customReaction
  2. concentrationwas concentrated
  3. custompurified by flash chromatography