93134-36-2

Upstream product

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

Downstream Products

• 753456-26-7 N⁶-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-2'-deoxyadenosine 
• 753456-22-3 N⁶-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-levulinyl-2'-deoxyadenosine 
• 753456-30-3 N⁶-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)]phosphinyl-2'-deoxyadenosine 
• 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 
• 93134-44-2 N⁴-Anisoyl-P-methyl-5'-O-dimethoxytrityl-2'-deoxycytidyl-(3'5')-N⁶-benzoyl-3'-O-levulinyl-2'-deoxyadenosine 
• 93134-46-4 4-Oxo-pentanoic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-({(2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yloxy}-methoxy-phosphoryloxymethyl)-tetrahydro-furan-3-yl ester 
• 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 

Relevant academic research and scientific papers

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

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.

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

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