反应 #74464

反应方程式

2,3,4,6-tetra-O-benzyl-D-glucopyranone

gluconolactone

compound 2

gluconolactone

(5-Bromo-2-chlorobenzyloxy)triisopropylsilane

compound 4

(5-Bromo-2-chlorobenzyloxy)triisopropylsilane

n-butyllithium

→

title compound

(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)-2-(4-chloro-3-((triisopropylsilyloxy)methyl)phenyl)-tetrahydro-2H-pyran-2-ol

溶剂

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   workup.STIRRINGthe mixture was stirred for 3 h at the same temperature
2. 2
   其他The reaction mixture was quenched by addition of saturated ammonium chloride solution
3. 3
   workup.ADDITIONAfter complete addition
4. 4
   其他The organic layer was separated
5. 5
   萃取the aqueous layer was extracted with ethyl acetate
6. 6
   洗涤The combined organic layers were washed with brine
7. 7
   干燥dried over magnesium sulfate
8. 8
   过滤filtered
9. 9
   浓缩concentrated in vacuo

实验过程

To a solution of (5-Bromo-2-chlorobenzyloxy)triisopropylsilane (compound 4, 97 g, 257 mmol) from Step 3 in tetrahydrofuran (1 L) at −78° C. under an atmosphere of nitrogen was added dropwise n-butyllithium (2.5 M in hexanes, 103 mL, 257 mmol), and the mixture was stirred for 1.5 h at the same temperature. Then a solution of 2,3,4,6-tetra-O-benzyl-D-glucopyranone (compound 2, 106 g, 198 mmol) from Step 1 in tetrahydrofuran (500 mL) was added dropwise, and the mixture was stirred for 3 h at the same temperature. The reaction mixture was quenched by addition of saturated ammonium chloride solution. After complete addition, the solution was gradually raised to room temperature. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to yield the title compound as a yellow oil which was used without further purification.

来源