반응 #808138

반응 방정식

water

N-acetyl-colchicinol

(2R,3R,4S,5R,6R)-2-[(5S)-5-(Acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl]oxy-3,5-bis(isobutyryloxy)-6-[(isobutyryloxy)methyl]tetrahydro-2H-pyran-4-yl 2-methylpropanoate

methyl dichlorophosphate

→

(5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl methyl hydrogen phosphate

수율 69.0%

용매

THF

THF

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 15 minutes
2. 2
   기타was removed by evaporation
3. 3
   기타After removal of the insoluble material
4. 4
   여과by filtration
5. 5
   기타the filtrate was purified on HP20 SS resin
6. 6
   세척eluting with a gradient of 0–60% methanol/water
7. 7
   기타The appropriate fractions were freeze-dried

실험 절차

A solution of N-acetyl-colchicinol (1) (0.45 g; 1.26 mmol) in THF (40 ml) under argon was cooled to 0° C. and treated with a 1.0M solution of lithiumHMDS in THF (1.39 ml; 1.39 mmol). The mixture was stirred at 0° C. for 1 hour and then added in portions over about 15 minutes to a solution of methyl dichlorophosphate (625 μl; 4.16 mmol) in THF (150 ml). The mixture was stirred at ambient temperature for 15 minutes. After addition of water (200 ml) the THF was removed by evaporation. After removal of the insoluble material by filtration, the filtrate was purified on HP20 SS resin eluting with a gradient of 0–60% methanol/water. The appropriate fractions were freeze-dried to give (5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl methyl hydrogen phosphate as white solid (391 mg).

출처