195375-62-3

Basic information

• Product Name: N-{9-[(2R,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(trityl-amino)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide
• Synonyms: N-{9-[(2R,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(trityl-amino)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide
• CAS NO: 195375-62-3
• Molecular Weight: 710.951
• Mol File: 195375-62-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-{9-[(2R,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(trityl-amino)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-{9-[(2R,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(trityl-amino)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide(195375-62-3)
• EPA Substance Registry System: N-{9-[(2R,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(trityl-amino)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide(195375-62-3)

Safety Data

• Hazardous Substances Data: 195375-62-3(Hazardous Substances Data)

Upstream product

• 76-83-5 trityl chloride 
• 195375-61-2 3'-amino-6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyadenosine 
• 125944-11-8 9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine 
• 59921-48-1 N-benzoyltetrazole 
• 1417713-27-9 C₃₅H₄₂N₆O₂Si 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 195375-63-4 N-benzoyl-2 ^{FontWeight=Bold FontSize=10} ',3'-dideoxy-3'-[(triphenylmethyl)amino]adenosine 
• 195375-58-7 Benzoic acid (2R,3R,5R)-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester 
• 195375-60-1 3'-azido-6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyadenosine 
• 195375-59-8 6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-3'-xylo-adenosine 
• 116597-14-9 N⁶-benzoyl-9-(3-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)adenine 

Downstream Products

• 195375-61-2 3'-amino-6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyadenosine 
• 195375-63-4 N-benzoyl-2 ^{FontWeight=Bold FontSize=10} ',3'-dideoxy-3'-[(triphenylmethyl)amino]adenosine 

Relevant articles and documents

OLIGONUCLEOTIDE COMPOSITIONS AND METHODS OF MAKING THE SAME

The present disclosure provides a solid phase method of making oligonucleotides via sequential coupling cycles including at least one coupling of a dinucleotide dimer subunit to a free 3'-terminal group of a growing chain. The oligonucleotides include at least two nucleoside subunits joined by a N3'→P5' phosphoramidate linkage. The method may include the steps of (a) deprotecting the protected 3' amino group of a terminal nucleoside attached to a solid phase support, said deprotecting forming a free 3' amino group; (b) contacting the free 3' amino group with a 3'-protected amino-dinucleotide-5'-phosphoramidite dimer in the presence of a nucleophilic catalyst to form an internucleoside N3'→P5' phosphoramidite linkage; and (c) oxidizing (e.g., sulfurizing) the linkage. The compositions produced by the subject methods may include a reduced amount of one or more (N-x) oligonucleotide products. Also provided are pharmaceutical compositions including the subject oligonucleotide compositions.

N3′→P5′ Oligodeoxyribonucleotide Phosphoramidates: A New Method of Synthesis Based on a Phosphoramidite Amine-Exchange Reaction

A new method for the synthesis of N3′→P5′ phosphoramidate oligodeoxynucleotides is demonstrated. Described herein is the synthesis of the monomers utilized in the phosphoramidite amine-exchange process and the experimental details pertaining to this new mode of chain assembly. The phosphoramidite amine-exchange method generates coupling yields in the 92-95% range per cycle and further enables the synthesis of chimeric phosphoramidate/phosphodiester or phosphoramidate/ phosphorothioate oligonucleotides with no instrument modifications.