Publication

Method for preparation of pentopyranosyl nucleosides

1999
Patents

Abstract

Title compds. consisting of ribo-, arabino-, xylo-, or lyxo-pyranoses in place of the usual ribo-furanose, were prepd. and used in solid-phase synthesis to construct (b-D-ribo)-(4'->2')-H-GGGCGGGC-H(I). Thus, 1,2,3,4-tetra-O-benzoyl-a/b-D-ribo-pyranose was substituted at the 1-position with a series of protected nucleoside bases, and the sugar manipulated through a series of steps to give either the 4'-O-dimethoxytrityl-3'-O-benzoyl-2'-O-(allyloxy)(diisopropyl-amino)phosphine compds. suitable for solid-phase synthesis of oligonucleotides, or 2'-O-CO(CH2)5CO2H compds. suitable for attachment to amine-resins to form the initial base of a growing chain. A key step in this synthesis was the simultaneous protection of 3'- and 4'-O by reaction with an aldehyde, ketone, acetal, or ketal protecting group to form cyclic acetals. These intermediates were then used in the construction of I. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/fa374362-9153-4ca2-b1d0-b83b4c0afb6d

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1999
Patents

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/fa374362-9153-4ca2-b1d0-b83b4c0afb6d

About this result

Related concepts (31)

Protecting group

A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In many preparations of delicate organic compounds, some specific parts of their molecules cannot survive the required reagents or chemical environments. Then, these parts, or groups, must be protected. For example, lithium aluminium hydride is a highly reactive but useful reagent capable of reducing esters to alcohols.

Acetal

In organic chemistry, an acetal is a functional group with the connectivity . Here, the R groups can be organic fragments (a carbon atom, with arbitrary other atoms attached to that) or hydrogen, while the R' groups must be organic fragments not hydrogen. The two R' groups can be equivalent to each other (a "symmetric acetal") or not (a "mixed acetal"). Acetals are formed from and convertible to aldehydes or ketones and have the same oxidation state at the central carbon, but have substantially different chemical stability and reactivity as compared to the analogous carbonyl compounds.

Hemiacetal

A hemiacetal or a hemiketal has the general formula R1R2C(OH)OR, where R1 or R2 is hydrogen or an organic substituent. They generally result from the addition of an alcohol to an aldehyde or a ketone, although the latter are sometimes called hemiketals. Most sugars are hemiacetals. According to the IUPAC definition, in R1R2C(OH)OR R1 and R2 may or may not be a hydrogen. In a hemiketal, neither R-group can be a hydrogen. Hemiketals are regarded as hemiacetals where none of the R-groups are H, and are therefore a subclass of the hemiacetals.

Related publications (3)

Method for preparation of pentopyranosyl nucleosides

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Reliable chemical synthesis of oligoribonucleotides (RNA) with 2'-O-[(triisopropylsilyl)oxy]methyl(2'-O-tom)-protected phosphoramidites

Specialists for RNA synthesis

Chemoselectively addressable HCan building blocks in peptide synthesis: L-homocanaline derivatives