Aminonucleosides and their Derivatives; VII¹. Synthesis of the 3′,5′-Dideoxy-3′,5′-diaminonucleosides

New Electronic Analogs of the Sialyl Cation: N-Functionalized 4-Acetamido-2,4-dihydroxypiperidines. Inhibition of Bacterial Sialidases

“…Reaction of ribo triflate 11 (obtained from 10 by reaction with triflic anhydride and pyridine) with sodium azide afforded the protected azide 12 in 85% yield from 10 . Unlike the reported reaction for the corresponding xylo triflate, no elimination products were observed . The xylo -configuration of azide 12 was established by X-ray crystallographic analysis of a diacetyl derivative…”

Synthesis and Properties of New Nucleotide Analogues Possessing Squaramide Moieties as New Phosphate Isosters

“…The key intermediates, the 3Ј,5Ј-diazido-3Ј,5Ј-dideoxynucleosides 28 and 29, were synthesized by the procedure reported by Gottikh, [19] with a slight modification. In our modified procedure, we employed bis(trifluoromethylsulfonyl) derivative 26 in place of the di(methylsulfonyl) derivative reported in the original procedure.…”

“…Compound 27 was further converted into the diazidonucleosides 28 and 29 by the original procedure. [19] The base moieties of 28 and 29 were protected with DMTr groups to give the DMTr derivatives 30 and 31, and the azide compounds were converted into the amino derivatives 32 and 33 by use of triphenylphosphane. In spite of the highly polar natures of the diamino structures of 32 and 33, they could be purified by silica gel column chromatography, because of the lipophilicity of the DMTr group.…”

Azidonucleosides: Synthesis, Reactions, and Biological Properties

“…266 The 3′,5′-diazidoribose 5.063 can be ob- derivatives 5.066, 5.067, and 5.068, respectively. 267 The monoazidosugar 5.069 was synthesized in excellent yield from 5.061. Pyrimidine derivatives 5.070 and 5.071 have been synthesized from the diacetates obtained from 5.069.…”