121058-83-1

Basic information

• Product Name: 5′-O-(dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-N⁶-phenoxyacetyladenosine
• Synonyms: 5′-O-(dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-N⁶-phenoxyacetyladenosine
• CAS NO: 121058-83-1
• Molecular Weight: 818.014
• Mol File: 121058-83-1.mol

Chemical Properties

• CAS DataBase Reference: 5′-O-(dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-N⁶-phenoxyacetyladenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 5′-O-(dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-N⁶-phenoxyacetyladenosine(121058-83-1)
• EPA Substance Registry System: 5′-O-(dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-N⁶-phenoxyacetyladenosine(121058-83-1)

Safety Data

• Hazardous Substances Data: 121058-83-1(Hazardous Substances Data)

Upstream product

• 10457-15-5 O^2'_,O3'_,O5'-tris-trimethylsilanyl-adenosine 
• 701-99-5 Phenoxyacetyl chloride 
• 119824-65-6 N⁶-phenoxyacetyladenosine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 58-61-7 adenosine 
• 17331-18-9 N'-[9-((3aR,4R,6R,6aR)-2-Dimethylamino-6-hydroxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-N,N-dimethyl-formamidine 
• 375345-66-7 phenoxyacetyl-1-O-benzotriazolide 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 121076-16-2 5'-O-dimethoxytrityl-N₆-phenoxyacetyladenosine 
• 57018-82-3 5'-O-dimethoxytrityladenosine 
• 121058-86-4 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 

Downstream Products

• 129395-58-0 C₅₀H₆₀N₇O₈PSSi 
• 121058-86-4 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 

Relevant articles and documents

THE USE OF LABILE BASE PROTECTING GROUPS IN OLIGORIBONUCLEOTIDE SYNTHESIS

The use of phenoxyacetyl group for the protection of the exocyclic amino function of purine bases and acetyl group for cytosine in oligonucleotide synthesis by the cyanoethylphosphoramidite approach is described.A side reaction - i.e. partial replacement of phenoxyacetyl group of protected guanines by acetyl group - was observed during the capping step.It can be avoided by the use of phenoxyacetic anhydride in place of acetic anhydride.

Nucleoside recovery in DNA and RNA synthesis

Nucleoside phosphoramidites and H-phosphonate diesters can be converted to nucleosides under mild conditions and in high yields by reaction with polyhydroxy alcohols.

High yield protection of purine ribonucleosides for phosphoramidite RNA synthesis

We report high yield procedures for protection of purine ribonucleosides based on a reaction which allows concomitant highly regiospecific 2'-silylation and 3'-phosphitylation. Subsequent cleavage of the H-phosphonate monoester moiety without silyl migration provides intermediates ready for phosphitylation by standard methods to give fully protected phosphoramidites.

CHEMICAL SYNTHESIS OF DIMER RIBONUCLEOTIDES CONTAINING INTERNUCLEOTIDIC PHOSPHORODITHIOATE LINKAGES

Ribonucleosides, chlorobis(amino)phosphines and thiols react via phosphorothioamidites to form phosphorothioites.Oxidation with sulphur gives ribonucleoside phosphorodithioate triesters which after deprotection yields the phosphorodithioate ribonucleoside