DMT-dC(bz) Phosphoramidite

Base Information

• Chemical Name: DMT-dC(bz) Phosphoramidite
• CAS No.: 102212-98-6
• Molecular Formula: C₄₆H₅₂N₅O₈P
• Molecular Weight: 833.921
• Hs Code.: 29349990
• European Community (EC) Number: 801-520-8
• DSSTox Substance ID: DTXSID50431406
• Nikkaji Number: J587.393B
• Mol file: 102212-98-6.mol

Synonyms:102212-98-6;DMT-dC(bz) Phosphoramidite;Bz-dC Phosphoramidite;5'-O-(4,4'-Dimethoxytrityl)-N4-benzoyl-2'-deoxycytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite;(2R,3S,5R)-5-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite;N4-Benzoyl-2'-deoxy-5'-O-DMT-cytidine 3'-CE phosphoramidite;DMT-dC(bz) Pharmadite(R);N-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide;DMT-dC(bz) Phosphoramidite, configured for ABI;DMT-dC(bz) Phosphoramidite, configured for MerMade;C46H52N5O8P;SCHEMBL1539812;DTXSID50431406;MFCD00036315;AKOS022179887;AC-9555;CS-W009565;HY-W008849;AS-15640;BP-28839;PD157992;D5701;D82189;A850131;5'-O-DMT-N4-Benzoyl-2'-Deoxycytidine-CE Phosphoramidite;DMT-dC(bz) Phosphoramidite, configured for ??KTA(R) and OligoPilot(R);(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite;(2R,3S,5R)-5-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-yl(2-cyanoethyl)diisopropylphosphoramidite;N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-cytidine 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite];Cytidine, N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-, 3'-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite];DMT-dC(bz) Phosphoramidite, configured for ABI, configured for (??KTA(R) and OligoPilot(R));N-Benzoyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine;N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-3'-[2-cyanoethyl N,N-bis(1-methylethyl) phosphoramidite] Cytidine

Chemical Property of DMT-dC(bz) Phosphoramidite

Chemical Property:

• Vapor Pressure: 0-0Pa at 20-50℃
• PKA: 8.65±0.20(Predicted)
• PSA: 159.99000
• Density: 1.23 at 20℃
• LogP: 8.54318
• Storage Temp.: Store at -20°C
• Solubility.: Chloroform, DMSO, Methanol (Slightly)
• 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:

99% ^*data from raw suppliers

N4-Benzoyl-2’-deoxy-5’-O-DMT-cytidine3’-CEPhosphoramidite ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

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=CC(=NC5=O)NC(=O)C6=CC=CC=C6
• 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=CC(=NC5=O)NC(=O)C6=CC=CC=C6
• Uses: 5'-O-DMT-N4-Benzoyl-2'-deoxycytidine 3'-CE phosphoramidite is used to prepare antisense oligonucleotides containing conformationally constrained methoxyaminomethylene and aminooxymethylene and aminomethylene bridged nucleoside analogs.

Technology Process of DMT-dC(bz) Phosphoramidite

There total 14 articles about DMT-dC(bz) 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%

→ 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)

Guidance literature:

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

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

Reference yield: 99.0%

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) + 4-N-Benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine (67219-55-0) → 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)

Guidance literature:

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite; 4-N-Benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine; In acetonitrile; at 20 ℃;

With 5-Phenyl-1H-tetrazole; In acetonitrile; at 20 ℃; for 5h; Product distribution / selectivity;

Reference yield: 81.0%

5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-O-[(2-cyanoethyl)-N,N-diisopropylphosphoramidite] (140613-57-6) + benzoyl chloride (98-88-4) → 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)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 26h;

DOI:10.1021/ol051949z

upstream raw materials:

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

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

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

5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-O-[(2-cyanoethyl)-N,N-diisopropylphosphoramidite]

Downstream raw materials:

Phosphoric acid (2R,3S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester; compound with ammonia

5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-O-[(2-cyanoethyl)-N,N-diisopropylphosphoramidite]

Refernces

• 1、 -. "ON-DEMAND PHOSPHORAMIDITE SYNTHESIS". Page/Page column 36-38; 48. . Retrieved 2022/01/24.
• 2、 Janczyk, Matthaeus,Appel, Bettina,Springstubbe, Danilo,Fritz, Hans-Joachim,Mueller, Sabine. "A new and convenient approach for the preparation of β-cyanoethyl protected trinucleotide phosphoramidites". . p. 1510 - 1513. Retrieved 2012/03/22.