N4-Benzoyl-3'-deoxy-5'-O-DMT-cytidine

Base Information

• Chemical Name: N4-Benzoyl-3'-deoxy-5'-O-DMT-cytidine
• CAS No.: 86234-45-9
• Molecular Formula: C37H35 N3 O7
• Molecular Weight: 633.69
• DSSTox Substance ID: DTXSID30543839
• Wikidata: Q82420801
• Mol file: 86234-45-9.mol

Synonyms:86234-45-9;N4-Benzoyl-3'-deoxy-5'-O-DMT-cytidine;N-[1-[(2R,3R,5S)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide;N4-benzoyl-5'-o-(dimethoxytrityl)-3'-deoxycytidine;DTXSID30543839;N-Benzoyl-5'-O-(dimethoxytrityl)-3'-deoxycytidine;W-203963;N-Benzoyl-5'-O-[bis(4-methoxyphenyl)(phenyl)methyl]-3'-deoxycytidine;N4-Benzoyl-3'-deoxy-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-cytidine;N-(1-((2R,3R,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide;N-[1-[(2R,3R,5S)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-3-hydroxy-tetrahydrofuran-2-yl]-2-oxo-pyrimidin-4-yl]benzamide

Chemical Property of N4-Benzoyl-3'-deoxy-5'-O-DMT-cytidine

Chemical Property:

• PSA: 121.14000
• LogP: 5.24290
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 633.24750046
• Heavy Atom Count: 47
• Complexity: 1080

Purity/Quality:

97% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)OCC4CC(C(O4)N5C=CC(=NC5=O)NC(=O)C6=CC=CC=C6)O
• Isomeric SMILES: COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)OC[C@@H]4C[C@H]([C@@H](O4)N5C=CC(=NC5=O)NC(=O)C6=CC=CC=C6)O

Technology Process of N4-Benzoyl-3'-deoxy-5'-O-DMT-cytidine

There total 34 articles about N4-Benzoyl-3'-deoxy-5'-O-DMT-cytidine 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: 90.0%

N-{1-[(2R,3R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide (86234-38-0) → N4-benzoyl-5'-O-dimethoxytrityl-3'-deoxyribicytidine (86234-45-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In ethanol;

DOI:10.1016/S0040-4039(00)81550-6

Reference yield: 85.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + N4-benzoyl-3'-deoxyribicytidine (161110-00-5) → N4-benzoyl-5'-O-dimethoxytrityl-3'-deoxyribicytidine (86234-45-9)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1081/NCN-100107190

Reference yield:

3'-deoxycytidine (7057-33-2) → N4-benzoyl-5'-O-dimethoxytrityl-3'-deoxyribicytidine (86234-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TMS-Cl / pyridine / 0.33 h / 20 °C

1.2: 82 percent / pyridine / 2 h / 20 °C

2.1: 85 percent / pyridine / 20 °C

With pyridine; chloro-trimethyl-silane; In pyridine;

DOI:10.1081/NCN-100107190

upstream raw materials:

4,4'-dimethoxytrityl chloride

N⁴-benzoyl-3'-deoxyribicytidine

N-{1-[(2R,3R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

benzoyl chloride

Downstream raw materials:

Acetic acid (2R,3R,5S)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-hydroxymethyl-tetrahydro-furan-3-yl ester

4-N-benzoyl-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine 2-cyanoethyl N,N-diisopropylphosphoramidite

Refernces

• 1、 Rhie,Pfleiderer. "Nucleosides. LVI. Synthesis and chemical modifications of 3'-deoxy- pyrimidine nucleosides". . p. 1425 - 1452. Retrieved 2007/10/02.