- Synthesis of acyclic nucleoside derivatives
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Methods and novel intermediates of the formula: wherein R6 and R7 are lower alkyl or benzyl or R6 and R7 taken together are —CH2CH2—, —CH2CH2CH2— or —CH2CH2CH2CH2CH2—, R8 is C1-C21 alkyl or a C2-C21 monounsaturated alkenyl, which may optionally be substituted with substitution substituents independently selected from the group consisting of hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkanoyl, amino, halo, cyano, azido, oxo, mercapto and nitro, and R9 is an alcohol protecting group. The intermediates are useful for the preparation of acyclic nucleoside derivatives of the formula: where one of R1 and R2 is an amino acid acyl group and the other of R1 and R2 is a —C(O)C3-C21 saturated or monounsaturated, optionally substituted alkyl and R3 is OH or H; or a pharmaceutically acceptable salt thereof.
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- Synthesis of optically active nucleoside analogs containing 2,3- dideoxyapiose in the presence of a catalytic amount of trimethylsilyl iodide
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Optically pure (R)-4,4-diethoxy-2-(hydroxymethyl)butyl acetate (1) was synthesized enantioselectively by lipase-catalyzed transesterification from 4,4-diethoxy-2-(hydroxymethyl)butanol. Coupling of silylated nucleobases and 2-O-acetyl-5-O-pivaloyl-(3S)-2,
- Ohsawa,Shiozawa,Achiwa,Terao
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p. 1906 - 1909
(2007/10/02)
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