A New Phosphorylating Reagent. V. The Preparation of α-Glycerophosphoryl Choline and Its Analogues by Means of 2-Chloromethyl-4-nitrophenyl Phosphorodichloridate
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概要
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β'-Haloethyl isopropylidene-α-glycerophosphoryl 2-chloromethyl-4-nitrophenyl phosphates (10 and 11) were prepared by the stepwise phosphorylations of ethylene halohydrin and 1,2-isopropylidene-glycerol with 2-chloromethyl-4-nitrophenyl phosphorodichloridate (3), a phosphorylating reagent having an "activatable" protecting group. The protecting group of 10 and 11 was readily and selectively removed by hydrolysis through an active intermediate 14 derived from the reaction of 10 and 11 with various tertiary amines to afford the corresponding isopropylidene-α-glyceryl β'-haloethylhydrogen phosphate (15) along with 2-hydroxy-5-nitrobenzyl trialkyl ammonium chloride (16), a chip of the active intermediate 14. The halogen atom in the ethyl chain of the phosphate 15 reacted with tertiary amine at the same time to afford the corresponding quaternary ammonium compound 17 which was converted by subsequent hydrolysis into α-glycerophosphoryl choline (1a) and its analogues (1b-d). Thus, DL-α-glycerophosphoryl choline (1a), its L-isomer (1a-L), inner salt of β'-(DL-α-glyceryl hydrogen phosphoroxy) ethyl triethyl ammonium hydroxide (1b), 1-[β'-(DL-α-glyceryl) hydrogen phosphoroxy] ethyl 1-methyl piperidinium hydroxide (1c) and inner salt of 1-[β'-(DL-α-glyceryl) hydrogen phosphoroxy] ethyl 1,4-diazonia bicyclo [2,2,2] octane hydroxide (1d) were prepared in good yield. DL-Myristoyl lecithin (18) was prepared by acylation of 1a with myristoyl chloride to confirm the structure of synthetic 1a.
- 1971-04-25
著者
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米田 直人
Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.
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米田 直人
Chemical Research & Development Laboratory, Tanabe Seiyaku & Co., Ltd.
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虫鹿 好孝
Chemical Research & Development Laboratory, Tanabe Seiyaku & Co., Ltd.
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虫鹿 好孝
Chemical Research & Development Laboratory Tanabe Seiyaku Co. Ltd.
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米田 直人
Research Laboratory of Applied Biochemistry Tanabe Seiyaku Co., Ltd.
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