7057-27-4Relevant articles and documents
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Suhadolnik,Uematsu
, p. 545 (1978)
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Preparation method of 3'-deoxyuridine
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, (2017/09/02)
The invention relates to the field of pharmaceutical synthesis and particularly relates to a preparation method of 3'-deoxyuridine. The method comprises the steps: by adopting a compound 3 as a raw material, firstly protecting amino through acetic anhydride to obtain a compound 4, obtaining a compound 5 under the action of acetyl bromide, reducing through a hypophosphite system to obtain a compound 6; removing deacetylated amino under the action of high-pressure water vapor and an organic solvent to obtain a compound 8 or removing N-acetyl to obtain a compound 7; and finally removing all acetyl to obtain a mixture of 3'-deoxyuridine and 3'-deoxycytidine; separating and purifying to obtain 3'-deoxyuridine crystal and 3'-deoxycytidine crystal separately, or directly removing all acetyl through the compound 6 to obtain the 3'-deoxycytidine. Available natural products are taken as initial raw materials, so that the method is simple in operation and convenient to purify, and industrial large-scale production is extremely easy to implement.
2′,3′-Anhydrouridine. A useful synthetic intermediate
Miah, Anwar,Reese, Colin B.,Song, Quanlai,Sturdy, Zoe,Neidle, Stephen,Simpson, Ian J.,Read, Martin,Rayner, Emma
, p. 3277 - 3283 (2007/10/03)
2,2′-Anhydro-1-(β-D-arabinofuranosyl)uracil 1 reacts with sodium hydride in dry DMSO to give 2′,3′-anhydrouridine 2. When the latter compound 2 is heated below its melting point or treated with triethylamine in methanol, it isomerises back to the 2,2′-anhydronucleoside 1. Treatment of compound 1 with sodium ethanethiolate or the sodium salt of benzyl mercaptan in the presence of an excess of the corresponding thiol in DMA gives 2′-S-ethyl-or 2′-S-benzyl-2′-thiouridine (4 or 11) in high yield; however, treatment of the 2,2′-anhydronucleoside 1 first with sodium hydride in DMA and then with a deficiency (with respect to sodium hydride) of ethanethiol or benzyl mercaptan gives the corresponding 3′-S-ethyl or 3′-S-benzyl derivative (3 or 12) in high yield. When the 2,2′-anhydronucleoside 1 is allowed to react with an excess of potassium tert-butoxide in DMSO, the 3′,5′-anhydronucleoside 13 is obtained in good yield. The latter compound 13 undergoes hydrolysis in aqueous trifluoroacetic acid to give 1-(β-D-xylofuranosyl)uracil 14 in high yield. The 3′-S-benzyl derivative 12 is converted by Raney nickel desulfurisation into 3′-deoxyuridine 15 which, in turn, is converted into 3′-deoxycytidine 17 in good yield. X-Ray crystallographic data relating to compounds 11 and 12 are also reported.
