93778-57-5

Basic information

• Product Name: 5'-O-(4,4'-dimethoxytrityl)-2'-deoxyinosine
• Synonyms: DMT-dI;5'-O-(4,4'-dimethoxytrityl)-2'-deoxyinosine;5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-deoxyinosine;2'-Deoxy-5'-O-DMT-inosine;5'-O-(4,4'-dimethoxytrityl)-2'-deoxy
• CAS NO: 93778-57-5
• Molecular Formula: C₃₁H₃₀N₄O₆
• Molecular Weight: 554.5931
• EINECS: 298-195-2
• Mol File: 93778-57-5.mol
• Article Data: 5

Chemical Properties

• Appearance: White to Pale Yellow/Powder
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 5'-O-(4,4'-dimethoxytrityl)-2'-deoxyinosine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4,4'-dimethoxytrityl)-2'-deoxyinosine(93778-57-5)
• EPA Substance Registry System: 5'-O-(4,4'-dimethoxytrityl)-2'-deoxyinosine(93778-57-5)

Safety Data

• Hazardous Substances Data: 93778-57-5(Hazardous Substances Data)

Usage

Uses

5''-O-(4,4''-Dimethoxytrityl)-2''-deoxyinosine

Upstream product

• 890-38-0 2-deoxyinosine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 1254223-76-1 (MeO)2Tr-OAc 
• 40615-35-8 4,4'-dimethoxytrityl alcohol 

Downstream Products

• 102304-77-8 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester methyl ester 
• 177779-54-3 Imidazole-1-carbothioic acid O-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl] ester 
• 527720-88-3 5'-O-dimethoxytrityl-1-(2,4-dinitrophenyl)-2'-deoxyinosine 
• 527720-90-7 5'-O-dimethoxytrityl-1-amino-2'-deoxyinosine 
• 527720-92-9 5'-O-dimethoxytrityl-N₁-(9-acridinecarboxyamino)-2'-deoxyinosine 
• 527720-94-1 5'-O-dimethoxytrityl-N₁-(1-pyreneacetylamino)-2'-deoxyinosine 
• 69655-05-6 Dideoxyinosine 
• 130676-58-3 5'-O-acetyl-2',3'-dideoxyinosine 
• 177779-55-4 9-{(2R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1,9-dihydro-purin-6-one 
• 1427172-86-8 5′-O-[bis(4-methoxyphenyl)(phenyl)methyl]-3′-O-mesyl-2′-deoxyinosine 
• 1402062-68-3 5′-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2-deoxy-3′-thioinosyl 3′-S-acetate 
• 1334533-59-3 5′-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2-deoxy-3′-thioinosine 
• 1334533-56-0 S-[5′-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2-deoxy-3′-thioinosinyl] O-(2-cyanoethyl) diisopropylamidothiophosphite 
• 1402062-64-9 5′-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2′-deoxy-xylo-inosine 

Relevant articles and documents

PRO-CYCLIC DINUCLEOTIDES AND PRO-CYCLIC DINUCLEOTIDE CONJUGATES FOR CYTOKINE INDUCTION

The present invention provides a Pro-cyclic dinucleotide (Pro-CDN) comprising a STING agonist cyclic dinucleotide which is coupled to a linker system. The Pro-CDNs of the present invention can be metabolized at a targeted site into CDNs and exert their full immunomodulatory effects at said targeted site. The present invention also provides conjugates wherein a Pro-CDN is conjugated to a Biologically Active Molecule (BAM) such as e.g. a cytotoxic molecule, a lipid, a protein, a peptide, a nucleic acid, a sugar or a PRR ligand. The invention provides also methods related to the use of such compounds to perform their activities at their targeted sites, to exert cytotoxic, cytostatic or immunomodulatory effects, to treat or to prevent diseases such as cancers, immunological disorders or infections.

Improved synthesis of 5-hydroxymethyl-2′-deoxycytidine phosphoramidite using a 2′-deoxyuridine to 2′-deoxycytidine conversion without temporary protecting groups

5-Hydroxymethylcytosine has recently been characterized as the 'sixth base' in human DNA. To enable research on this DNA modification, we report an improved method for the synthesis of 5-hydroxymethyl-2′-deoxycytidine (5-HOMedC) phosphoramidite for site-specific incorporation into oligonucleotides. To minimize manipulations we employed a temporary protecting group-free 2′-deoxyuridine to 2′-deoxycytidine conversion procedure that utilizes phase transfer catalysis. The desired 5-HOMedC phosphoramidite is obtained in six steps and 24% overall yield from 2′-deoxyuridine.

Synthesis and Properties of Phosphoramidite Derivatives of Modified Nucleosides

Protected N6-methyl-2'-deoxyadenosine (d-m6A), 2-amino-2'-deoxyadenosine (d-a2A), 2'-deoxyinosine (dI), 5-methyl-2'-deoxycytidine (d-m5C) and deoxyuridine (dU) were reacted with bis(diisopropylamino)methoxyphosphine in the presence of diisopropylammonium tetrazolide as the activating reagent to give the corresponding phosphoramidite derivatives in yields of 100, 65, 90, 78 and 65 percent respectively.The 31P-nuclear magnetic resonance spectra of the products were measured.Using these compounds, dinucleotides and trinucleotides were synthesized on a longchain alkylamine controlled pore glass (LCA-CPG) in quantitative yields.The stability of 6-methyldeoxyadenosine and N,N-diisobutyryl-2-aminodeoxyadenosine to acid was examined.When protected di- and trinucleotides (m6A-T, a2A-T, T-m6A-T, T-a2A-T) bound to the support (LCA-CPG) were treated with 3 percent trichloroacetic acid in dichloromethane, depurination was negligible within 10 min (dinucleotide) or 60 min (trinucleotide).Keywords - phosphoramidite; solid-phase synthesis; phosphite method; acid treatment; enzyme degradation