85231-45-4

Upstream product

• 4546-72-9 N₆-benzoyl-2'-deoxyadenosine 
• 647834-80-8 O-levulinyl acetonoxime 
• 123-76-2 levulinic acid 
• 591-12-8 5-methyl-2-furanone 
• 64325-78-6 N₆-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine 
• 40608-06-8 levulinic anhydride 

Downstream Products

• 87007-45-2 Phosphoric acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester methyl ester 
• 199436-70-9 C₆₆H₆₄Cl₂N₁₁O₁₄PS 
• 93134-58-8 N⁶-Benzoyl-P-methyl-5'-O-dimethoxytrityl-2'-deoxyadenosyl-(3'5')-N⁴-benzoyl-2'-deoxycytidine 
• 181645-22-7 (R)-Octyl-phosphonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 181787-30-4 (S)-Octyl-phosphonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 224298-18-4 5'-O-(N⁶-benzoyl-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-β-cyanoethyl phosphorothioate 

Relevant academic research and scientific papers

Direct regioselective enzymatic acylation of nucleosides: Building-blocks for the solution phase synthesis of oligonucleotides

The synthesis of 3′- and 5′-O-levulinyl nucleosidic monomers through enzymatic acylation with acetonoxime levulinate is demonstrated. The acylation process takes place in one-step and use of expensive reagents, such as DMTrCl is avoided. The regioselectiv

Process Development of Biocatalytic Regioselective 5′-O-Levulinylation of 2′-Deoxynucleosides

An enzymatic process was optimized for regioselective levulinylation of the 5′-hydroxyl group in 2′-deoxynucleosides. The results revealed that the nucleobase protecting group influenced the successful outcome of the enzymatic reaction. The enhanced solubility of 4-tert-butylphenoxyacetyl protected 2′-deoxynucleoside played a major role during acylation reaction enabling the starting nucleosides to be the best substrates for Candida antarctica lipase B. Furthermore, we have developed a packed column protocol as a superior alternative to batch process carried-out in a flask, particularly when scale-up is required. The industrial application of this method was demonstrated via the synthesis of 5′-O-levulinylthymidine on a 25 g scale.

Enzymatic parallel kinetic resolution of mixtures of d / l 2′-deoxy and ribonucleosides: An approach for the isolation of β- L -nucleosides

We have developed a lipase-catalyzed parallel kinetic resolution of mixtures of β-d/l-nucleosides. The opposite selectivity during acylation exhibited by Pseudomonas cepacia lipase (PSL-C) with β-d- and β-l-nucleosides furnished acylated compounds that have different R f values. As a consequence, isolation of both products was achieved by simple column chromatography. Computer modeling of the transition-state analogues during acylation of β-d- and β-l-2′-deoxycytidine with PSL-C was carried out to explain the high selectivity. PSL-C favored the 3′-O-levulination of the β-d enantiomer, whereas the 5′-OH group was acylated in 2′-deoxy-β-l-cytidine. In both cases, the cytosine base was placed in the alternate hydrophobic pocket of PSLs substrate-binding site, where it can form extra hydrogen bonds (in addition to the five essential catalytically relevant hydrogen bonds) that stabilize these intermediates catalyzing the selective acylation of β-d/l-nucleosides.

2,2,5,5-Tetramethylpyrrolidin-3-one-1-sulfinyl group for 5′-hydroxyl protection of deoxyribonucleoside phosphoramidites in the solid-phase preparation of DNA oligonucleotides

Several nitrogen-sulfur reagents have been investigated as potential 5′-hydroxyl protecting groups for deoxyribonucleoside phosphoramidites to improve the synthesis of oligonucleotides on glass microarrays. Out of the nitrogen-sulfur-based protecting grou

Novel enzymatic synthesis of levulinyl protected nucleosides useful for solution phase synthesis of oligonucleotides

An efficient synthesis of 3′- and 5′-O-levulinyl-2′- deoxy- and 2′-O-alkylribonucleosides has been developed from appropriate nucleosides by enzyme-catalyzed regioselective acylation in organic solvents. Several lipases were screened in combination with a

Process for the synthesis of oligomeric compounds

Synthetic processes are provided wherein oligomeric compounds are prepared having phosphodiester, phosphorothioate, and phosphorodithioate covalent linkages. Also provided are synthetic intermediates useful in the processes.

Oligodeoxyribonucleotide phosphorothioates: Substantial reduction of (N- 1)-mer content through the use of trimeric phosphoramidite synthons

Use of fully protected trimeric phosphoramidite synthons in the synthesis of oligonucleotide phosphorothioate shows a substantial reduction (>85%) in (n-1)-mer content as compared to oligomers synthesized through coupling of standard phosphoramidite monom

The H-phosphonate approach to the synthesis of oligonucleotides and their phosphorothioate analogues in solution

A new approach to the synthesis of oligonucleotides and oligonucleotide phosphorothioates in solution is described; it is based on H-phosphonate coupling [with bis(2-chlorophenyl) phosphorochloridate 22 as the coupling agent] at -40 deg C, followed by in situ sulfur transfer involving either 2-(4-chlorophenylsulfanyl)isoindole-1,3(2H)-dione 23a or 4-[(2-cyanoethyl)sulfanyl]morpholine-3,5-dione 26. The yields of the coupling and sulfur transfer reactions are virtually quantitative and, following unblocking by previously reported procedures, very pure products (d[ApC], d[TpGpApC], d[TpGp(s)ApC], d[Gp(s)A] and d[Cp(s)Tp(s)Gp(s)A]) are obtained.

Synthesis and duplex stability of oligodeoxynucleotides containing stereoregular or stereorandom octylphosphonate linkages

The synthesis of oligodeoxynucleotide pentadecamers containing two octylphosphonate linkages [3'-O-P(=O)(n-C8H17)-O-5'] with stereoregular or stereorandom chirality is described. The introduction of random octylphosphonate linkages was performed using a monomeric nucleoside octylphosphonamidite as synthon whereas the introduction of stereoregular linkages could be accomplished by the use of stereoregular dimers containing a preformed octylphosphonate linkage. The novel oligodeoxynucleotides were characterized by electrospray ionization mass spectrometry and the influence of chirality of the modified linkages on the duplex stability was studied. Furthermore, end-capped oligodeoxynucleotides having two octylphosphonate linkages at either end which were directed against HSV-1 mRNA have been synthesized for investigation as antisense drugs.

Improvements in Oligodeoxyribonucleotide Synthesis: Methyl N,N-Dialkylphosphoramidite Dimer Units for Solid Support Phosphite Methodology

Two procedures for the synthesis of methyl N,N-dialkylphosphoramidite dinucleotides (dimer units) compatible with the current solid support phosphite methodology of oligodeoxynucleotide synthesis are described for the first time.In the first procedure a c