- Method for synthesizing zidovudine azide intermediate based on continuous flow micro-reaction technology
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The method comprises the following steps: (1) mixing a zidovudine oxygen bridge, a nitriding reagent and a solvent, dissolving a zidovudine oxygen bridge and a azide reagent in the solvent to prepare a reaction raw material solution. (2) The reaction raw material solution is fed into a microchannel reactor for reaction to obtain a product solution containing a zidovudine azide intermediate. By adopting the micro-channel reactor as the core reaction equipment, continuous nitriding reaction can be carried out, the dosage of the nitriding reagent is reduced, the reaction rate is accelerated, and the reaction risk is reduced.
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Paragraph 0057-0086
(2021/10/05)
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- Intermediate preparation zidovudines and method
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Disclosed is a method for preparing zidovudine (B). The method comprises the following steps: 1) 2'-halothymidine (A) is used as the raw material to obtain a compound of formula (I) by protecting the hydroxyl group thereof in the 5'-position; 2) the compound of formula (I) is subjected to the acylation of the hydroxyl group in the 3'-position to obtain a compound of formula (VI); 3) the compound of formula (VI) is dehalogenated to obtain a compound of formula (111); 4) the compound of formula (III) is subjected to an elimination reaction to obtain a compound of formula (IV); 5) the compound of formula (IV) is subjected to an azidation reaction to obtain a compound of formula (V); and 6) the compound of formula (V) is deprotected to obtain zidovudine (B); the specific reaction formula being shown in (C)below. In the formulae: X is a halogen, P1 is a protecting group for hydroxyl; and P2 is C1-C4 alkylsulfonyl, fluoro-C1-C4 alkylsulfonyl, arylsulfonyl or -CS-R, wherein R is C1-C4 alkyl.
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- Serendipitous discovery of a zidovudine guanidine complex: A superior process for the production of zidovudine
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A superior process for the commercial production of zidovudine (AZT) has been developed. It was discovered that an AZT-guanidine complex formed when a crude zidovudine solution was treated with guanidine. This readily precipitated from protic solvents resulting in the exclusion of impurities and permitted the development of a superior isolation and purification of AZT.
- Radatus, Bruno K.
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p. 1281 - 1286
(2012/01/13)
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- A simple one-pot procedure for the direct conversion of alcohols into azides using TsIm
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A facile and efficient method for one-pot conversion of alcohols into azides using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, alcohols are refluxed with a mixture of NaN3, TsIm and triethylamine in the presence of catalytic amounts of tetra-n-butylammonium iodide (TBAI) in DMF affording the corresponding alkyl azides in good yields. This methodology is highly efficient for various structurally diverse alcohols with selectivity for ROH: 1° > 2° > 3°.
- Soltani Rad, Mohammad Navid,Behrouz, Somayeh,Khalafi-Nezhad, Ali
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p. 3445 - 3449
(2008/02/10)
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- An efficient F-18 labeling method for PET study: Huisgen 1,3-dipolar cycloaddition of bioactive substances and F-18-labeled compounds
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The Cu(I)-catalyzed, 1,3-dipolar cycloaddition reaction was applied successfully to the synthesis of small, F-18-labeled biomolecules, and an optimal condition was developed for one-pot, two-step reaction without any interim purifications. This technique was employed in various F-18-labeled, 1,2,3-triazole syntheses with high radiochemical yield.
- Sirion, Uthaiwan,Kim, Hee Jun,Lee, Jae Hak,Seo, Jai Woong,Lee, Byoung Se,Lee, Sang Ju,Oh, Seung Jun,Chi, Dae Yoon
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p. 3953 - 3957
(2008/02/04)
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- An efficient synthesis of 3′-amino-3′-deoxythymidine derivatives
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An efficient method of reduction of 3′-azido-3′-deoxythymidine and its 5′-protected derivatives to 3′-aminothymidine derivatives on a palladium catalyst using ammonium formate as a source of hydrogen was suggested.
- Seregin,Chudinov,Yurkevich,Shvets
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p. 135 - 138
(2007/10/03)
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- Solid-phase synthesis of positively charged deoxynucleic guanidine (DNG) oligonucleotide mixed sequences
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Positively charged DNG oligonucleotide mixed sequences containing A/T bases were prepared by solid-phase synthesis. Synthesis proceeds in 3′→5′ direction and involves coupling of 3′-Fmoc protected thiourea in the presence of HgCl2/TEA with the corresponding 5′-amine of the growing oligo chain. DNG binding characteristics with complementary DNA and with itself have been evaluated.
- Reddy, Putta Mallikarjuna,Bruice, Thomas C.
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p. 1281 - 1285
(2007/10/03)
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- Uracil- and thymine-substituted thymidine and uridine derivatives
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The four possible 3'-uracil-1-yl and 3'-thymin-1-yl derivatives of 3'- deoxythymidine and the four analogous derivatives of 2'-deoxyuridine have been synthesised from thymidine and uridine, respectively. Advantages of the 2-(methoxycarbonyl)vinyl group to prevent the formation of anhydronucleosides and SnCl2/PhSH/Et3N in relation to H2/Pd for the reduction of most azido groups are disclosed.
- Costa, Anna M.,Faja, Montserrat,Farras, Jaume,Vilarrasa, Jaume
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p. 1835 - 1838
(2007/10/03)
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- Synthesis and biological activity of 3'-azido- and 3'-amino substituted nucleoside analogs
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The product distribution obtained in the reaction of 1-(5-0-trityl-0-mesyl-2-deoxy-β-D-erythro-pentofuranosyl)-2,4-(1H, 3H)-pyrimidinedione with lithium azide in N, N'-dimethylformamide at 100°C depends on the nature of the substituent in 5. The results may be explained by a difference in the acidity of the pyrimidinedione. The reaction of the more acidic nucleosides (X = I, F) appears to proceed preferentially through the 2,3'-anhydro intermediate, whereas for the less acidic products (X = H, CH3) direct nucleophilic displacement by the azide ion predominates. The different 3'-azidfo derivatives were reduced to 3'-amino compounds. All 3'-azido- and 3'-aminopyrimidine nucleosides were tested against herpes simplex virus, vaccinia and vesicular stomatitis virus and on murine L1210 cell growth. None of the substances exhibited significant activity.
- Colla,Herdewijn,De Clercq,et al.
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p. 295 - 301
(2007/10/02)
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- One-Step Synthesis of 5'-Azido-nucleosides
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Regioselective azidation of unprotected or appropriately protected nucleosides was conducted by means of the reagent triphenylphosphine-carbon tetrabromide-lithium azide.By use of this reagent, 5'-azido-5'-deoxynucleosides were prepared conveniently in one step from nucleosides in high yields.Secondary hydroxy-groups of appropriately 5'-protected nucleosides were also converted by the reagent to azido-functions with complete inversion.
- Yamamoto, Isamu,Sekine, Mitsuo,Hata, Tsujiaki
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p. 306 - 310
(2007/10/02)
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- Nucleosides. 115. Reaction of 3'-O-Mesylthymidine. Formation of 1-(3-Azido-2,3-dideoxy-β-D-threo-pentofuranosyl)thymine and Its Conversion into 6,3'-Imino-1-(2,3-dideoxy-β-D-threo-pentofuranosyl)thymine
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Treatment of 5'-O-trityl-3'-O-mesylthymidine (3) with NaN3 in DMF at reflux gave 5'-O-trityl-3'-azido-3'-deoxythymidine (5) and 6,3'-imino-1-(5-O-trityl-3-deoxy-β-D-threo-pentofuranosyl)thymine (8).Compound 8 was formed from the 3'-azido-threo-pentofuranosylthymine derivative 6.A mechanism is proposed for the formation of 8 from 6.Also, the 6,5'-imino-bridged thymidine 18 was prepared.Conformational features of these imino-bridged nucleosides are discussed.
- Matsuda, Akira,Watanabe, Kyoichi A.,Fox, Jack J.
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p. 3274 - 3278
(2007/10/02)
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