反应 #216248

反应方程式

(R)-3-(t-butyldimethylsiloxy)tetradecanal

Z-glycine

potassium hydrogen sulphate

diisopropylamine

n-butyllithium

→

(2R/S,3R/S,5R)-2-[1-(benzyloxy)formamido]-5-(t-butyldimethylsiloxy)-3-hydroxyhexadecanoic acid

收率 47.9%

溶剂

THF

THF

THF

hexane

反应条件

后处理

1. 1
   workup.WAITThe reaction mixture was left
2. 2
   温度to warm to room temperature
3. 3
   温度again cooled to -75° C
4. 4
   workup.STIRRINGThe reaction mixture was stirred at -75° C. for 1 hour and at -40° to -50° C. for 1/2 hour
5. 5
   温度warmed to 5° C.
6. 6
   温度again cooled to -75° C.
7. 7
   萃取extracted with ether
8. 8
   干燥The ether phase was dried
9. 9
   浓缩concentrated
10. 10
    其他chromatographed on silica gel with methylene chloride/methanol

实验过程

A solution of 3.0 ml of diisopropylamine in 50 ml of THF was treated at 0° C. with 12.0 ml of a solution of 1.6M n-butyllithium in hexane and, after stirring, cooled to -75° C. A solution of 1.26 g of Z-glycine in 10 ml of THF was then added dropwise. The reaction mixture was left to warm to room temperature and again cooled to -75° C. 0.7 g of (R)-3-(t-butyldimethylsiloxy)tetradecanal in 5 ml of THF was then added dropwise at -75° C. The reaction mixture was stirred at -75° C. for 1 hour and at -40° to -50° C. for 1/2 hour, then warmed to 5° C., again cooled to -75° C., poured into dilute potassium hydrogen sulphate solution and extracted with ether. The ether phase was dried, concentrated and chromatographed on silica gel with methylene chloride/methanol. There were obtained 540 mg of (2R/S,3R/S,5R)-2-[1-(benzyloxy)formamido]-5-(t-butyldimethylsiloxy)-3-hydroxyhexadecanoic acid as a mixture of 4 diastereomers.

来源