The present invention relates to efficient processes useful in the preparation of fluorinated nucleosides, such as (2S,3R,4S,5R)-5-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-3-fluoro-4-hydroxy-2-(mercaptomethyl)tetrahydrofuran-3-yl dihydrogen phosphate, also known as 3′-fluoro-thio-guanosine monophosphate or 3′-F-thio-GMP. Such fluorinated nucleosides may be useful as a biologically active compound and or as an intermediate for the synthesis of more complex biologically active compounds. The present invention also encompasses intermediates useful in the disclosed synthetic processes and the methods of their preparation. (I)

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The present disclosure provides 3′ protected nucleotides, including those 3′ protected nucleotides having a detectable tag. Systems and methods of sequencing nucleic acids using the 3′ protected nucleotides are also disclosed, such as the sequencing of a nucleic acid using a nanopore or the sequencing of a nucleic acid via sequencing-by-synthesis.

The present disclosure provides nucleoside compounds and oligonucleotides including an unnatural 6-amino-2-pyridone heterocyclic base where the 6-amino and 2-positions are protected. The 2-position of the heterocyclic base can be protected with an acyl-oxy-methyl protecting group. In some embodiments, the protected heterocyclic base has the following structure where AcOM is an acetyl-oxy-methyl group and R is a ribose or deoxyribose sugar: ##STR00001## Methods for synthesizing an oligonucleotide are provided in which the subject compounds find use. The method can include protecting an unnatural (e.g., Z) nucleotide with an acetyl-oxy-methyl group; incorporating the protected unnatural nucleotide into a nucleotide sequence on a solid support; and removing the acetyl-oxy-methyl group from the unnatural nucleotide incorporated into the nucleotide sequence. The compounds and methods find use in the synthesis of long oligonucleotides including Z nucleotides.

The present disclosure provides nucleoside compounds and oligonucleotides including an unnatural 6-amino-2-pyridone heterocyclic base where the 6-amino and 2-positions are protected. The 2-position of the heterocyclic base can be protected with an acyl-oxy-methyl protecting group. In some embodiments, the protected heterocyclic base has the following structure where AcOM is an acetyl-oxy-methyl group and R is a ribose or deoxyribose sugar: ##STR00001## Methods for synthesizing an oligonucleotide are provided in which the subject compounds find use. The method can include protecting an unnatural (e.g., Z) nucleotide with an acetyl-oxy-methyl group; incorporating the protected unnatural nucleotide into a nucleotide sequence on a solid support; and removing the acetyl-oxy-methyl group from the unnatural nucleotide incorporated into the nucleotide sequence. The compounds and methods find use in the synthesis of long oligonucleotides including Z nucleotides.

Disclosed are halogenated 2-deoxy-lactone, 2′-deoxy-nucleosides, and derivatives thereof, for example, a compound of formula (I). Also disclosed are a composition comprising a pharmaceutically acceptable carrier and at least one compound or salt of the invention, and a method of treating a disorder is selected from the group consisting of an abnormal cellular proliferation, a viral infection, and an autoimmune disorder. ##STR00001##

Disclosed are halogenated 2-deoxy-lactone, 2′-deoxy-nucleosides, and derivatives thereof, for example, a compound of formula (I). Also disclosed are a composition comprising a pharmaceutically acceptable carrier and at least one compound or salt of the invention, and a method of treating a disorder is selected from the group consisting of an abnormal cellular proliferation, a viral infection, and an autoimmune disorder. ##STR00001##

The present invention relates to methods for the synthesis of fondaparinux and intermediates thereto.

The present invention relates to methods for the synthesis of fondaparinux and intermediates thereto.

The invention provides synthetic processes and synthetic intermediates that can be used to prepare compounds having useful anti-HIV properties.

The invention provides synthetic processes and synthetic intermediates that can be used to prepare compounds having useful anti-HIV properties.