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

Base Information

• Chemical Name: Cytidine, N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-, 3'-(2-cyanoethyl phosphonate)
• CAS No.: 152998-05-5
• Molecular Formula: C40H39N4O9P
• Molecular Weight: 750.745
• Mol file: 152998-05-5.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 12 articles about Cytidine, N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-, 3'-(2-cyanoethyl phosphonate) 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%

N4-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3-O-[O-(2-cyanoethyl)-N,N-(diisopropyl)]phosphoramidite (116003-04-4,116003-05-5,141847-24-7,102212-98-6,130794-98-8,130794-99-9) → N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-cytidine 3'-(2-cyanoethylphosphonate) (152998-05-5)

Guidance literature:

N₄-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3-O-[O-(2-cyanoethyl)-N,N-(diisopropyl)]phosphoramidite; With 1H-tetrazole; In acetonitrile; at 20 ℃; for 0.166667h;

With water; In acetonitrile; at 20 ℃; for 0.5h; Further stages.;

DOI:10.1021/ol0166045

Reference yield:

N2-isobutyryl-3'-O-levulinyl-2'-deoxyguanosine (93134-41-9) + N4-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3-O-[O-(2-cyanoethyl)-N,N-(diisopropyl)]phosphoramidite (116003-04-4,116003-05-5,141847-24-7,102212-98-6,130794-98-8,130794-99-9) → 5'-O-DMTr-dCBzpsCNEdGi-Bu-3'-O-Lev (656249-30-8) + N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-cytidine 3'-(2-cyanoethylphosphonate) (152998-05-5)

Guidance literature:

N²-isobutyryl-3'-O-levulinyl-2'-deoxyguanosine; N₄-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3-O-[O-(2-cyanoethyl)-N,N-(diisopropyl)]phosphoramidite; With poly(4-vinylpyridinium-p-toluenesulfonate); In dichloromethane; at 20 ℃; for 6h;

With poly(4-vinylpyridinium-p-toluenesulfonate); water; In dichloromethane; for 0.5h;

With pyridine; Amberlyst A-26 tetrathionate; In dichloromethane; at 20 ℃; for 11h; Title compound not separated from byproducts;

DOI:10.1021/ol0511777

Reference yield:

N2-isobutyryl-3'-O-levulinyl-2'-deoxyguanosine (93134-41-9) + N4-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3-O-[O-(2-cyanoethyl)-N,N-(diisopropyl)]phosphoramidite (116003-04-4,116003-05-5,141847-24-7,102212-98-6,130794-98-8,130794-99-9) → C59H62N9O15P + N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-cytidine 3'-(2-cyanoethylphosphonate) (152998-05-5)

Guidance literature:

N²-isobutyryl-3'-O-levulinyl-2'-deoxyguanosine; N₄-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3-O-[O-(2-cyanoethyl)-N,N-(diisopropyl)]phosphoramidite; With poly(4-vinylpyridinium-p-toluenesulfonate); In dichloromethane; at 20 ℃; for 6h;

With poly(4-vinylpyridinium-p-toluenesulfonate); water; In dichloromethane; for 0.5h; Title compound not separated from byproducts;

DOI:10.1021/ol0511777

upstream raw materials:

N₄-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3-O-[O-(2-cyanoethyl)-N,N-(diisopropyl)]phosphoramidite

N²-isobutyryl-3'-O-levulinyl-2'-deoxyguanosine

5'-OH-dTps_CNEdT-3'-O-Lev

5'-OH-dA^Bzps_CNEdT-3'-O-Lev

Downstream raw materials:

5'-(4,4'-dimethoxytrityl)-N⁴-benzoyl-2'-deoxycytidine-3'-H-phosphonate

4-N-Benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine

Refernces

• 1、 Coppola, Cinzia,Simeone, Luca,De Napoli, Lorenzo,Montesarchio, Daniela. "On the compatibility of azides in phosphoramidite-based couplings: Synthesis of a novel, convertible azido-functionalized CyPLOS analogue". experimental part. p. 1155 - 1165. Retrieved 2011/04/15.
• 2、 Padiya, Kamlesh J.,Mohe, Nikhil U.,Salunkhe, Manikrao M.. "Solid phase oligonucleotide synthesis by using β-CE H-phosphonate approach". . p. 917 - 922. Retrieved 2007/10/03.