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HRID580022

反应详情

EQUATION

反应方程式

HRID 580022 的结构方程式

REACTANTS

反应物

2
结构：CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O
HCID2734143

α-Acetobromogalactose

C14H19BrO9

结构：F.[F-].[K+]
HCID11829350

Potassium fluoride (K(HF2)​)

HF2K

PRODUCTS

生成物

1
结构：CC(=O)OC[C@H]1O[C@@H](F)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O
HCID11078616

β-D-Galactopyranosyl fluoride, 2,3,4,6-tetraacetate

C14H19FO9

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CC#N
溶剂HCID6342

Acetonitrile

C2H3N

PROCEDURE

实验过程

10.0 g (24.3 mmol) of 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide were heated under reflux in 100 ml of anhydrous acetonitrile with 10.0 g (128 mmol) of potassium hydrogen difluoride for 6 hours. The mixture was then filtered, the solvent was stripped off in vacuo and the residue was taken up in methylene chloride. After filtration over a short silica gel column and concentration of the solution, it was possible to crystallize the product from ether. Yield 6.1 g (72%), melting point 100° C., [α·D20 =+17.5 (c=1.03 in CHCl3) [F. Micheel et al., Chem. Ber. 88, 475 (1955), melting point 98°-99° C., [α]D18 =+22 (CH3OH)]. 1H NMR (CDCl3): δ=5.26 (dd, 1-H), J1.2 =7.0, J1,F =50.0 Hz.

WORKUP

后处理

  1. filtrationThe mixture was then filtered
  2. filtrationAfter filtration over a short silica gel column and concentration of the solution, it
  3. customto crystallize the product from ether