Cytidine, N-benzoyl-3'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-, 5'-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite]

Base Information

• Chemical Name: Cytidine, N-benzoyl-3'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-, 5'-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite]
• CAS No.: 140712-83-0
• Molecular Formula: C₄₆H₅₂N₅O₈P
• Molecular Weight: 833.921
• European Community (EC) Number: 689-912-3
• DSSTox Substance ID: DTXSID801103447
• Nikkaji Number: J1.176.331F
• Mol file: 140712-83-0.mol

Synonyms:140712-83-0;(N4-BENZOYL)-5'-O-[(N,N-DIISOPROPYLAMINO)-(2-CYANOETHOXY)PHOSPHINYL]-3'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYCYTIDINE;Cytidine, N-benzoyl-3'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-, 5'-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite];SCHEMBL7202966;DTXSID801103447;AKOS037621789;F90248

Chemical Property of Cytidine, N-benzoyl-3'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-, 5'-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite]

Chemical Property:

• PKA: 8.66±0.20(Predicted)
• PSA: 159.99000
• LogP: 8.54318
• XLogP3: 7.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 19
• Exact Mass: 833.35535063
• Heavy Atom Count: 60
• Complexity: 1440

Purity/Quality:

97% ^*data from raw suppliers

N4-Benzoyl-2'-deoxy-3'-O-DMT-cytidine 5'-CE phosphoramidite ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N(C(C)C)P(OCCC#N)OCC1C(CC(O1)N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3)OC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC
• Isomeric SMILES: CC(C)N(C(C)C)P(OCCC#N)OC[C@@H]1[C@H](C[C@@H](O1)N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3)OC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC

Technology Process of Cytidine, N-benzoyl-3'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-, 5'-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite]

There total 7 articles about Cytidine, N-benzoyl-3'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-, 5'-[2-cyanoethyl N,N-bis(1-methylethyl)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:

4,4'-dimethoxytrityl chloride (40615-36-9) → α-<(N4-Benzoyl)-5'-O-<(N,N-diisopropylamino)(2-cyanoethoxy)phosphinyl>-3'-O-(di-p-methoxytrityl)-2'-deoxycytidine (140712-83-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 12 h / Ambient temperature

2: n-Bu₄NF / tetrahydrofuran / 2 h / 22 °C

3: N,N-diisopropylammonium tetrazolide / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; N,N-diisopropylamine tetrazolide; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00111a009

Reference yield:

N4-benzoyl-2'-deoxycytidine (4836-13-9) → α-<(N4-Benzoyl)-5'-O-<(N,N-diisopropylamino)(2-cyanoethoxy)phosphinyl>-3'-O-(di-p-methoxytrityl)-2'-deoxycytidine (140712-83-0)

Guidance literature:

Multi-step reaction with 6 steps

1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1.) 22 deg C, 1 h, 2.) r.t., 24 h

2: NaHCO₃ / methanol

3: imidazole / dimethylformamide

4: pyridine / 12 h / Ambient temperature

5: n-Bu₄NF / tetrahydrofuran / 2 h / 22 °C

6: N,N-diisopropylammonium tetrazolide / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; 1H-imidazole; N,O-bis-(trimethylsilyl)-acetamide; N,N-diisopropylamine tetrazolide; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00111a009

Reference yield:

N-[2-Oxo-1-((4S,5R)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1,2-dihydro-pyrimidin-4-yl]-benzamide → α-<(N4-Benzoyl)-5'-O-<(N,N-diisopropylamino)(2-cyanoethoxy)phosphinyl>-3'-O-(di-p-methoxytrityl)-2'-deoxycytidine (140712-83-0)

Guidance literature:

Multi-step reaction with 5 steps

1: NaHCO₃ / methanol

2: imidazole / dimethylformamide

3: pyridine / 12 h / Ambient temperature

4: n-Bu₄NF / tetrahydrofuran / 2 h / 22 °C

5: N,N-diisopropylammonium tetrazolide / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; 1H-imidazole; N,N-diisopropylamine tetrazolide; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00111a009

upstream raw materials:

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

α-(N⁴-Benzoyl)-3'-O-(di-p-methoxytrityl)-2'-deoxycytidine

4,4'-dimethoxytrityl chloride

N₄-benzoyl-2'-deoxycytidine

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