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HRID2055857

反应详情

EQUATION

反应方程式

HRID 2055857 的结构方程式

REACTANTS

反应物

2
结构：CC1(C)OC[C@H]2O[C@@H]3OC(C)(C)O[C@@H]3[C@H]2O1
HCID30337

alpha-D-Xylofuranose, 1,2:3,5-bis-O-(1-methylethylidene)-

C11H18O5

结构：O=C[C@H](O)[C@@H](O)[C@H](O)CO
HCID644160

未命名化合物

PRODUCTS

生成物

1
结构：CC1(C)O[C@H]2O[C@H](CO)[C@H](O)[C@H]2O1
HCID88338

.alpha.-D-Xylofuranose, 1,2-O-(1-methylethylidene)-

C8H14O5

收率 70.1%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：O=S(=O)(O)O
溶剂HCID1118

Sulfuric acid

H2O4S

PROCEDURE

实验过程

1,2:3,5-Di-O-isopropylidene-D-xylofuranose (70.66 g, 0.30 mol) is treated with H2SO4 (0.1 M, 300 mL). Upon stirring, the xylose slowly dissolves. After 30 minutes, the reaction is quenched with NH4OH (pH 9.0) and half of the water removed at reduced pressure. The aqueous layer is diluted with brine (100 mL) and extracted with ethyl acetate (3×200 mL). A normal work-up provides an oil. Kugelrohr distillation provides 1,2-O-isopropylidene-D-xylofuranose (40 g, 68.5%); b.p. 120-135° C./0.4 mm Hg.

WORKUP

后处理

  1. customthe reaction is quenched with NH4OH (pH 9.0) and half of the water
  2. customremoved at reduced pressure
  3. additionThe aqueous layer is diluted with brine (100 mL)
  4. extractionextracted with ethyl acetate (3×200 mL)
  5. customA normal work-up provides an oil
  6. distillationKugelrohr distillation