5'-O-(4,4'-Dimethoxytrityl)-N6-benzoyl-2'-deoxyadenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Base Information

• Chemical Name: 5'-O-(4,4'-Dimethoxytrityl)-N6-benzoyl-2'-deoxyadenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
• CAS No.: 98796-53-3
• Molecular Formula: C47H52 N7 O7 P
• Molecular Weight: 857.946
• Hs Code.: 29349990
• European Community (EC) Number: 685-521-7
• DSSTox Substance ID: DTXSID501103329
• Nikkaji Number: J587.394K
• Mol file: 98796-53-3.mol

Synonyms:Adenosine,N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-, 3'-[2-cyanoethylbis(1-methylethyl)phosphoramidite] (9CI)

Chemical Property of 5'-O-(4,4'-Dimethoxytrityl)-N6-benzoyl-2'-deoxyadenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Chemical Property:

• Vapor Pressure: 0-0Pa at 20-50℃
• PKA: 7.87±0.43(Predicted)
• PSA: 168.70000
• Density: 1.23 at 20℃
• LogP: 9.12618
• Storage Temp.: Store at -20°C
• Solubility.: soluble, clear
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 19
• Exact Mass: 857.36658402
• Heavy Atom Count: 62
• Complexity: 1380

Purity/Quality:

97% ^*data from raw suppliers

N6-Benzoyl-2’-deoxy-5’-O-DMT-cytidine3’-CEPhosphoramidite ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)N(C(C)C)P(OCCC#N)OC1CC(OC1COC(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)C4=CC=C(C=C4)OC)N5C=NC6=C(N=CN=C65)NC(=O)C7=CC=CC=C7
• Isomeric SMILES: CC(C)N(C(C)C)P(OCCC#N)O[C@H]1C[C@@H](O[C@@H]1COC(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)C4=CC=C(C=C4)OC)N5C=NC6=C(N=CN=C65)NC(=O)C7=CC=CC=C7
• Uses: N6-Benzoyl-2’-deoxy-5’-O-DMT-cytidine 3’-CE Phosphoramidite is used to prepare antisense oligonucleotides containing conformationally constrained methoxyaminomethylene and aminooxymethylene and aminomethylene bridged nucleoside analogs.

Technology Process of 5'-O-(4,4'-Dimethoxytrityl)-N6-benzoyl-2'-deoxyadenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

There total 10 articles about 5'-O-(4,4'-Dimethoxytrityl)-N6-benzoyl-2'-deoxyadenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

→ N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine-3'-O-[O-(2-cyanoethyl)-N,N'-diisopropylphosphoramidite] (98796-53-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene; for 0.0833333h;

With dmap; In dichloromethane; toluene; for 0.133333h;

Reference yield: 98.0%

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) + N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine (64325-78-6) → N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine-3'-O-[O-(2-cyanoethyl)-N,N'-diisopropylphosphoramidite] (98796-53-3)

Guidance literature:

With chloro-trimethyl-silane; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1039/a701924f

Reference yield: 92.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine (64325-78-6) → N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine-3'-O-[O-(2-cyanoethyl)-N,N'-diisopropylphosphoramidite] (98796-53-3)

Guidance literature:

N₆-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine; With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.166667h;

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine; With 1-hexyl-1-methylimidazoliumtris(pentafluoroethyl)trifluorophosphate; for 1.75h;

DOI:10.1039/b905000k

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

N₆-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

2-cyanoethoxy(N,N-diisopropylamino)3-nitro-1,2,4-triazolylphosphine

Downstream raw materials:

d(ApT)

N⁶-(benzoyl)-2'-deoxyadenosine 3'-(allyl 2-cyanoethyl phosphate)

N-benzyl-(3H-imidazo[2,1-i]purin-7-yl)methylamine

Refernces

• 1、 -. "BICYCLIC PEPTIDE LIGAND STING CONJUGATES AND USES THEREOF". Paragraph 00549. . Retrieved 2020/08/28.
• 2、 Hardacre, Christopher,Huang, Haifeng,James, Stuart L.,Migaud, Marie E.,Norman, Sarah E.,Pitner, William R.. "Overcoming hydrolytic sensitivity and low solubility of phosphitylation reagents by combining ionic liquids with mechanochemistry". supporting information; experimental part. p. 5846 - 5848. Retrieved 2011/06/26.