104992-55-4

Basic information

• Product Name: N-Benzoyl-5'-O-(4,4-Dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]adenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
• Synonyms: 2’-TBDMS-rA(N-Bz) Phosphoramidite;5'-O-DMT-2'-TBDMS-rA(N-Bz)-3'-CEDPA;N-Benzoyl-5'-O-(4,4-Dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]adenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite;(2R,3R,4R,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-(tert-butyldimethylsilyloxy)tetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite;REF DUPL: 2'-TBDMS-rA(N-Bz)Phosphoramidite;Bz-rA Phosphoramidite;N6-Benzoyl-2'-O-tert-butyldimethylsilyl-5'-O-DMT-adenosine 3'-CE phosphoramidite;5'-O-(4,4'-DiMethoxy)-N6-benzoyl-2'-O-(t-butyl diMethylsilyl)adenosine-3'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoraMidite
• CAS NO: 104992-55-4
• Molecular Formula: C₅₃H₆₆N₇O₈PSi
• Molecular Weight: 988.205
• EINECS: 2017-001-1
• Mol File: 104992-55-4.mol
• Article Data: 8

Chemical Properties

• Appearance: white to off-white/
• Storage Temp.: ?20°C
• PKA: 7.87±0.43(Predicted)
• CAS DataBase Reference: N-Benzoyl-5'-O-(4,4-Dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]adenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzoyl-5'-O-(4,4-Dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]adenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite(104992-55-4)
• EPA Substance Registry System: N-Benzoyl-5'-O-(4,4-Dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]adenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite(104992-55-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 104992-55-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 104992-55-4 differently. You can refer to the following data:
1. N-Benzoyl-5'-O-(4,4-Dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]adenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite can be used as Organic synthesis intermediates and pharmaceutical intermediates are mainly used in laboratory research and development processes and chemical production processes.
2. DMT-2''O-TBDMS-rA(bz) Phosphoramidite is a 2''-O-Protected ribonucleoside phosphoramidite used as a key raw material for the automated solid-supported synthesis of oligonucleotide-based drugs. It is also used to synthesize 2''-O-guanidinopropyl-modified nucleoside phosphoramidites to incorporate into siRNAs targeting hepatitis B virus.

Synthesis

To a solution of 72 (12.0 g, 15.2 mmoi) in DIPEA (15 ml) and DCM (30 niL’) is added DMAP (744 mg, 6.09 rnrnol) and 2cyanoethyl JV.Ndiisopropylchlorophosphoramidite (5.41 g, 22.9 rnmoi) at 25 °C. After stirring for 2 hours, the mixture is purified directly by basic silica gel column chromatography (EAIPE 1/4 toi/1) to give A2 as a white solid (13.0 g. 86% yield)

Upstream product

• 129666-75-7 6-N-benzoyl-5'-O-(4,4'-dimethoxytrityl)adenosine 
• 4546-55-8 N-benzoyladenosine 
• 1348775-39-2 adenosine 
• 98-88-4 benzoyl chloride 
• 102691-36-1 N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite 
• 129681-71-6 5'-O-dimethoxytrityl-2'-O-tert-butyldimethylsilyl-N₆-benzoyl adenosine 
• 124482-92-4 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine 

Relevant articles and documents

CYCLIC DI-NUCLEOTIDE COMPOUNDS AND METHODS OF USE

Disclosed are cyclic-di-nucleotide cGAMP analogs, methods of synthesizing the compounds, pharmaceutical compositions comprising the compounds thereof, and use of compounds and compositions in medical therapy.

Methods of producing phosphitylated compounds

Provided are methods of producing phosphitylated compounds, including 3′-O-phosphoramidites, comprising the step of reacting a hydroxyl-containing compound with a phosphitylating agent in the presence of a phosphitylation activator selected from the group consisting of: (1) acid-base complexes derived from an amine base of Formula I 1wherein R, R1, and R2 are independently C1-C10 alkyl, C1-C10 cycloalkyl, C1-C10 aryl, C1-C10 aralkyl, C1-C10 heteroalkyl, or C1-C10 heteroaryl; (2) acid-base complexes derived from an amine base of Formula II 2wherein R3, R4, R5, R6, and R7 are independently hydrogen, C1-C10 alkyl, C1-C10 cycloalkyl, C1-C10 aryl, C1-C10 aralkyl, C1-C10 heteroalkyl, or C1-C10 heteroaryl, and at least one of R3, R4, R5 R6, and R7 is not hydrogen.; (3) acid-base complexes derived from a diazabicyclo amine base; (4) zwitterionic amine complexes; and (5) combinations of two or more thereof, to produce a phosphitylated compound.

Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives

The present invention provides methods for the chemical synthesis of nucleosides and derivatives thereof, including 2′-amino, 2′-N-phthaloyl, 2′-O-methyl, 2′-O-silyl, 2′-O-triisopropylsilyloxymethyl, 2′-OH nucleosides, C-nucleosides, nucleoside phosphoramidites, C-nucleoside phosphoramidites, and non-nucleoside derivatives.