The present invention provides stereoselective processes of manufacture for the phosphoramidate nucleotide Compound 1 or a pharmaceutically acceptable salt thereof.

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Processes for the preparation of phosphorylated heptose compounds are provided. Embodiments of the invention relate to the chemical synthesis of heptopyranose phosphate compounds. Also, embodiments of the invention relate to the use of compounds according to the invention in modulating an immune response in a subject.

The present invention relates to an oligonucleotide comprising at least one phosphorodithioate internucleoside linkage of formula (I) (I) as defined in the description and in the claim. The oligonucleotide of the invention can be used as a medicement.

##STR00001##

The syntheses of two phosphoramidite building blocks based on BNSF and BNSMB structures are disclosed. Furthermore, some common molecular intermediates have been designed and linked to the central biphenyl core of the two molecules, resulting in a versatile and cost-effective design. These compounds can be effectively introduced to DNA oligonucleotides via the well-established standard cyanoethylphosphoramidite chemistry on the nucleic acid synthesizer. Fragmentation of these BNSF- and BNSMB-functionalized DNA strands is achieved by both one-photon and two-photon photolysis of photoliable bonds of [2-(2-nitrophenyl)propoxy]carbonyl groups on BNSF and BNSMB molecules respectively, resulting in two short pieces of single-stranded DNAs. The versatile design and facile synthesis of these two-photon photocleavage phosphoramidite molecules are beneficial to synthetic chemists and photochemists for the development of new caged compounds which enables to introduce into oligonucleotides as light-triggered carriers via solid-phase synthesis for a wide range of applications in materials science, polymer, chemistry, biology and DNA nanoecthnology.

The present invention provides apparatuses and methods for the synthesis of oligonucleotides and related compounds. In particular, the present invention allows to effectively prepare reagents to be fed into an apparatus for the synthesis of such oligomers.

The present invention provides apparatuses and methods for the synthesis of oligonucleotides and related compounds. In particular, the present invention allows to effectively prepare reagents to be fed into an apparatus for the synthesis of such oligomers.

The invention provides a compound of formula (I): ##STR00001##
wherein R is as described herein. The invention also provides a process for the preparation of the compound.

The invention provides a compound of formula (I): ##STR00001##
wherein R is as described herein. The invention also provides a process for the preparation of the compound.

The present invention relates to new synthetic molecules with agonist activity of human Toll-like Receptor 4 (TLR4), compositions comprising them and uses thereof for the treatment of diseases in which it is useful to induce or increase an immune response. The compounds have general formula (1), wherein R.sub.1 is a saturated C.sub.8-C.sub.16 aliphatic chain having a ═0 on C.sub.1, said chain being free from —OH substituents on C.sub.3, wherein R.sub.2 is a saturated C.sub.8-C.sub.16 aliphatic chain having a ═O on C.sub.1, said chain being free from —OH substituents on C.sub.3, wherein R.sub.3 is a saturated C.sub.8-C.sub.16 aliphatic chain having a ═O on C.sub.1, said chain being free from —OH substituents on C.sub.3; wherein R.sub.4 is a hydrogen atom (H) or a phosphate group (PO.sub.4.sup.2−).

##STR00001##

The present invention relates to new synthetic molecules with agonist activity of human Toll-like Receptor 4 (TLR4), compositions comprising them and uses thereof for the treatment of diseases in which it is useful to induce or increase an immune response. The compounds have general formula (1), wherein R.sub.1 is a saturated C.sub.8-C.sub.16 aliphatic chain having a ═0 on C.sub.1, said chain being free from —OH substituents on C.sub.3, wherein R.sub.2 is a saturated C.sub.8-C.sub.16 aliphatic chain having a ═O on C.sub.1, said chain being free from —OH substituents on C.sub.3, wherein R.sub.3 is a saturated C.sub.8-C.sub.16 aliphatic chain having a ═O on C.sub.1, said chain being free from —OH substituents on C.sub.3; wherein R.sub.4 is a hydrogen atom (H) or a phosphate group (PO.sub.4.sup.2−).

##STR00001##