93134-36-2

Upstream product

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

Downstream Products

• 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 
• 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 
• 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 
• 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 
• 753456-22-3 N⁶-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-levulinyl-2'-deoxyadenosine 
• 753456-26-7 N⁶-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-2'-deoxyadenosine 

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

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