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HRID580023

反应详情

EQUATION

反应方程式

HRID 580023 的结构方程式

REACTANTS

反应物

3
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
HCID11069632

2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranosyl bromide

C14H19BrO9

结构：F.[F-].[K+]
HCID11829350

Potassium fluoride (K(HF2)​)

HF2K

结构：CCOCC.ClCCl
HCID21881112

未命名化合物

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
HCID11268124

2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranosyl fluoride

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

8.7 g (21.2 mmol) of 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide were dissolved in 30 ml of anhydrous acetonitrile and the solution was heated under reflux with 5.0 g (64 mmol) of potassium hydrogen difluoride. After 3 hours, the starting material was no longer detectable (TLC: methylene chloride/ether, 9:1). The solution was filtered and concentrated and the crude product was recrystallized from ether. Yield 5.74 g (77%), melting point 65°-67° C., [α]D20 =+21.2 (c=1.07 in chloroform) [A. Bertho, loc. cit.: melting point 68°-69° C., [α]DS20 =+21.5 (chloroform)]. 1H NMR (CDCl3): δ=5.58 (dd, 1-H), J1,2 =1.9, J1,F =48.4 Hz; [L. D. Hall et al., Can. J. Chem. 47, 1 (1969): δ=5.57 (dd, 1-H), J1.2 =1.7, J1,F =48.6 Hz].

WORKUP

后处理

  1. temperaturethe solution was heated
  2. filtrationThe solution was filtered
  3. concentrationconcentrated
  4. customthe crude product was recrystallized from ether