Nebularine CEP

Base Information

• Chemical Name: Nebularine CEP
• CAS No.: 151132-95-5
• Molecular Formula: C46H61N6O7PSi
• Molecular Weight: 869.083
• Mol file: 151132-95-5.mol

Synonyms:NEBULARINE CEP;2-O-tert-Butyldimethylsilyl-5-O-DMT-nebularine 3-CE phosphoramidite

Chemical Property of Nebularine CEP

Chemical Property:

Purity/Quality:

98%Min ^*data from raw suppliers

2'-O-tert-Butyldimethylsilyl-5-O-DMT-nebularine 3'-CE phosphoramidite ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 2''-O-tert-Butyldimethylsilyl-5-O-DMT-nebularine 3''-CE phosphoramidite is used in preparation of cyclic Dinucleotide compounds as modulators of sting.

Technology Process of Nebularine CEP

There total 7 articles about Nebularine CEP 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: 79.3%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + 9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purine (151132-94-4) → 9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) (151132-95-5)

Guidance literature:

With 1-methyl-1H-imidazole; 2,3,5-trimethyl-pyridine; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2094::AID-HLCA2094>3.0.CO;2-H

Reference yield:

6-thioinosine (574-25-4) → 9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) (151132-95-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 79 percent / Raney-Ni / H₂O / 6 h / Heating

2: 84.7 percent / pyridine / 7 h / 20 °C

3: 53.2 percent / AgNO₃ / pyridine; tetrahydrofuran / 14 h

4: 79.3 percent / collidine; 1-methyl-1H-imidazole / acetonitrile / 2 h / 20 °C

With pyridine; 1-methyl-1H-imidazole; 2,3,5-trimethyl-pyridine; nickel; silver nitrate; In tetrahydrofuran; pyridine; water; acetonitrile; 1: Reduction / 2: Condensation / 3: Silylation / 4: Phosphitylation;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2094::AID-HLCA2094>3.0.CO;2-H

Reference yield:

2',3',5'-tri-O-benzoylinosine (6741-88-4) → 9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) (151132-95-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 90.4 percent / Lawesson's reagent / pyridine / 6 h / Heating

2: 85.4 percent / NaOH / pyridine; methanol / 0.08 h / 20 °C

3: 79 percent / Raney-Ni / H₂O / 6 h / Heating

4: 84.7 percent / pyridine / 7 h / 20 °C

5: 53.2 percent / AgNO₃ / pyridine; tetrahydrofuran / 14 h

6: 79.3 percent / collidine; 1-methyl-1H-imidazole / acetonitrile / 2 h / 20 °C

With Lawessons reagent; pyridine; 1-methyl-1H-imidazole; 2,3,5-trimethyl-pyridine; sodium hydroxide; nickel; silver nitrate; In tetrahydrofuran; pyridine; methanol; water; acetonitrile; 1: Thionation / 2: Hydrolysis / 3: Reduction / 4: Condensation / 5: Silylation / 6: Phosphitylation;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2094::AID-HLCA2094>3.0.CO;2-H

upstream raw materials:

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

9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purine

6-thioinosine

2',3',5'-tri-O-benzoylinosine