- Preparation method for emtricitabine isomer
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The invention discloses a preparation method for an embritabine isomer. The preparation method comprises the following steps: with Solketal as a starting material, allowing the Solketal to undergo a six-step reaction of esterification, hydrolysis, oxidation, condensation cyclization, acetylation and glycosylation condensation so as to synthesize four mixture intermediates of emtricitabine; and splitting the four isomer intermediates into a cis-isomer mixture and a trans-isomer mixture through a chiral reagent. According to the invention, by adoption of a simple starting material, a mixture forsplitting key intermediates of four optical isomers of the emtricitabine is synthesized through the six-step reaction, and chiral acid is utilized to split the four isomers into a mixture of cis andtrans isomers, so the preparation method provided by the invention has the advantages of simple and convenient operation, high yield and high isomer chiral purity.
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- Multienzymatic cascade synthesis of an enantiopure (2R,5R)-1,3-oxathiolane anti-HIV agent precursor
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An enantiopure (2R,5R)-1,3-oxathiolane was obtained using a multienzymatic cascade protocol. By employing a combination of surfactant-treated subtilisin Carlsberg and Candida antarctica lipase B, the absolute configuration of the resulting 1,3-oxathiolane ring was efficiently controlled, resulting in an excellent enantiomeric excess (>99%). This enantiopure 1,3-oxathiolane derivative is a key precursor to anti-HIV agents, such as lamivudine, through subsequent N-glycosylation.
- Ren, Yansong,Hu, Lei,Ramstr?m, Olof
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- Efficient asymmetric synthesis of lamivudine via enzymatic dynamic kinetic resolution
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The anti-HIV nucleoside lamivudine was asymmetrically synthesized in only three steps via a novel surfactant-treated subtilisin Carlsberg-catalyzed dynamic kinetic resolution protocol. The enantiomer of lamivudine could also be accessed using the same protocol catalyzed by Candida antarctica lipase B.
- Hu, Lei,Schaufelberger, Fredrik,Zhang, Yan,Ramstroem, Olof
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supporting information
p. 10376 - 10378
(2013/10/22)
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- PROCESS FOR THE MANUFACTURE OF CIS(-)-LAMIVUDINE
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An improved process for the manufacture of Lamivudine. The process involves: (a) resolution of racemic lamivudine (intermediate of formula IX) to cis (±) lamivudine of formula (XII) by forming a crystalline salt and separating the product from an organic solvent by fractional crystallization; (b) resolution of cis (±) lamivudine to cis (?) isomer involving formation of S-Binol adduct of formula XIV.
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- Facile preparation of α-acyloxyacetaldehyde, a versatile intermediate in the synthesis of antiviral nucleosides
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This report describes a novel and simple method for the preparation of a versatile intermediate, α-acyloxyacetaldehyde and its acetals, and its application to the synthesis of 4-acetoxy-2-acyloxymethyl-1,3-oxathiolane, an important intermediate in the syn
- Du, Jinfa,Watanabe, Kyoichi A.
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p. 1925 - 1930
(2007/10/03)
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- Preparation of intermediates useful in the synthesis of antiviral nucleosides
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The present invention is an efficient process for the manufacture of α-acyloxyacetaldehyde, a key intermediate in the synthesis of 1,3-oxathiolane and 1,3-dioxolane nucleosides.
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- PROCESS FOR PREPARING SUBSTITUTED 1,3-OXATHIOLANES WITH ANTIVIRAL PROPERTIES
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Disclosed are processes for preparing compounds of formula (I) and pharmaceutically acceptable salts or esters thereof, wherein R2 is a purine or pyrimidine base or an analogue or derivative thereof; and Z is S, S = O or SO2. The invention also relates to
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- Processes for preparing substituted 1,3-oxathiolanes with antiviral properties
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Disclosed are processes for preparing compounds of the formula (I) and pharmaceutically acceptable salts or esters thereof: STR1 wherein R2 is a purine or pyrimidine base or an analogue or derivative thereof; and Z is S, S=O or SO2.
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