3'-Cytidylic acid, N-benzoyl-2'-deoxy-, 2-chlorophenyl 2-cyanoethyl ester

Base Information

• Chemical Name: 3'-Cytidylic acid, N-benzoyl-2'-deoxy-, 2-chlorophenyl 2-cyanoethyl ester
• CAS No.: 80817-38-5
• Molecular Formula: C25H24 Cl N4 O8 P
• Molecular Weight: 574.914
• European Community (EC) Number: 279-566-8
• DSSTox Substance ID: DTXSID601148207
• Nikkaji Number: J320.320D
• Mol file: 80817-38-5.mol

Synonyms:80817-38-5;EINECS 279-566-8;3'-Cytidylic acid, N-benzoyl-2'-deoxy-, 2-chlorophenyl 2-cyanoethyl ester;LUODOPHROFJGEI-MRRPNWGVSA-N;DTXSID601148207

Chemical Property of 3'-Cytidylic acid, N-benzoyl-2'-deoxy-, 2-chlorophenyl 2-cyanoethyl ester

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 574.1020284
• Heavy Atom Count: 39
• Complexity: 1040

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3)CO)OP(=O)(OCCC#N)OC4=CC=CC=C4Cl
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3)CO)OP(=O)(OCCC#N)OC4=CC=CC=C4Cl

Technology Process of 3'-Cytidylic acid, N-benzoyl-2'-deoxy-, 2-chlorophenyl 2-cyanoethyl ester

There total 9 articles about 3'-Cytidylic acid, N-benzoyl-2'-deoxy-, 2-chlorophenyl 2-cyanoethyl ester 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:

N-4-benzoyl-5'-O-(dimethoxytrityl)-2'-deoxycitidine 3'-(o-chlorophenyl β-cyanoethyl phosphate) (80817-35-2) → N4-benzoyl-2'-deoxycytidine-3'-O-(2-chlorophenyl-2-cyanoethyl)phosphate (80817-38-5)

Guidance literature:

With zinc dibromide; In dichloromethane; isopropyl alcohol; Ambient temperature; var.: EtOAc, triazole, molecular sieves or BSA, CHCl₃, MeOH, 0 deg C, 6 min;

DOI:10.1016/S0040-4039(01)82014-1

Reference yield:

2-chlorophenyl phosphordi(1H-1-[1,2,4]triazolide) (72351-28-1) → N4-benzoyl-2'-deoxycytidine-3'-O-(2-chlorophenyl-2-cyanoethyl)phosphate (80817-38-5)

Guidance literature:

Multi-step reaction with 3 steps

1: dioxane / 2 h / 20 °C

2: 1-methylimidazole / dioxane / 3 h / 20 °C

3: benzenesulfonic acid / CHCl₃; methanol / 0.25 h / 0 °C

With benzenesulfonic acid; 1-methyl-1H-imidazole; In 1,4-dioxane; methanol; chloroform;

DOI:10.1002/hlca.19820650803

Reference yield:

[1,2,4]Triazol-1-yl-phosphonic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester (76964-04-0) → N4-benzoyl-2'-deoxycytidine-3'-O-(2-chlorophenyl-2-cyanoethyl)phosphate (80817-38-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-methylimidazole / dioxane / 3 h / 20 °C

2: benzenesulfonic acid / CHCl₃; methanol / 0.25 h / 0 °C

With benzenesulfonic acid; 1-methyl-1H-imidazole; In 1,4-dioxane; methanol; chloroform;

DOI:10.1002/hlca.19820650803

upstream raw materials:

N-4-benzoyl-5'-O-(dimethoxytrityl)-2'-deoxycitidine 3'-(o-chlorophenyl β-cyanoethyl phosphate)

3-Hydroxypropionitrile

2'-deoxycytidine monohydrochloride

2-chlorophenyl phosphordi(1H-1-[1,2,4]triazolide)

Downstream raw materials:

C₅₉H₅₅Cl₂N₅O₁₇P₂*C₆H₁₅N

C₆₃H₆₀Cl₂N₈O₁₇P₂

N-benzoyl-5'-O-(bis(4-methoxyphenyl)phenylmethyl)-P-(2-chlorophenyl)-2'-deoxycytidylyl-(3'->5')-N-benzoyl-2'-deoxy-3'-cytidylic acid, 2-chlorophenyl 2-cyanoethyl ester

C₆₆H₆₃Cl₂N₉O₁₇P₂

Refernces

• 1、 Ohtsuka,Iwai,Tokunaga,Ikehara. "Deoxyribonucleic acids (DNA) and related compounds. XIII. Synthesis of DNA duplexes containing a ribosome binding site". . p. 3153 - 3159. Retrieved 2007/10/02.
• 2、 Kierzek, R.,Ito, H.,Bhatt, R.,Itakura, K.. "SELECTIVE N-DEACYLATION OF N,O-PROTECTED NUCLEOSIDES BY ZINC BROMIDE". . p. 3761 - 3764. Retrieved 2007/10/02.