N4-Benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxycytidine

Base Information

• Chemical Name: N4-Benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxycytidine
• CAS No.: 51549-36-1
• Molecular Formula: C22H31 N3 O5 Si
• Molecular Weight: 445.591
• European Community (EC) Number: 894-614-3
• Mol file: 51549-36-1.mol

Synonyms:N4-BENZOYL-5'-O-TERT-BUTYLDIMETHYLSILYL-2'-DEOXYCYTIDINE;51549-36-1;5-O-TBDMS-N4-Benzoyl-2-deoxycytidine;MFCD04972284;N-[1-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide;SCHEMBL7034452;CCPOWNJNXQQIFV-YQVWRLOYSA-N;AKOS037621701;AC-32245;PD157762;HY-138593;CS-0159258;N-(1-((2R,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

Chemical Property of N4-Benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxycytidine

Chemical Property:

• PSA: 102.68000
• LogP: 3.23880
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 445.20329763
• Heavy Atom Count: 31
• Complexity: 740

Purity/Quality:

98%,99%, ^*data from raw suppliers

N4-Benzoyl-5''-O-tert-butyldimethylsilyl-2''-deoxycytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCC1C(CC(O1)N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3)O
• Isomeric SMILES: CC(C)(C)[Si](C)(C)OC[C@@H]1[C@H](C[C@@H](O1)N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3)O

Technology Process of N4-Benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxycytidine

There total 11 articles about N4-Benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxycytidine 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: 84.0%

tert-butyldimethylsilyl chloride (18162-48-6) + N4-benzoyl-2'-deoxycytidine (4836-13-9) → N-(1-((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide (51549-36-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.1080/15257771003708579

Reference yield: 30.0%

tert-butyldimethylsilyl chloride (18162-48-6) + N4-benzoyl-2'-deoxycytidine (4836-13-9) → N-(1-((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide (51549-36-1) + N4-benzoyl-O3',O5'-bis(tert-butyldimethylsilyl)-2'-deoxycytidine (51549-38-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1021/jo01311a061

Reference yield:

2'-Deoxycytidine (951-77-9) → N-(1-((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide (51549-36-1)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 15 h / 80 °C

2: 49 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; In pyridine; N,N-dimethyl-formamide;

DOI:10.1021/jo01311a061

upstream raw materials:

tert-butyldimethylsilyl chloride

N₄-benzoyl-2'-deoxycytidine

pentachlorophenyl benzoate

pentafluorophenyl benzoate

Downstream raw materials:

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

5'-O-tert-butyldimethylsilyl-3'-O,4-N-dibenzoyl-2'-deoxycytidine

Refernces

• 1、 Lucas,Teste,Zerrouki,Champavier,Guilloton. "Chelation-controlled regioselective alkylation of pyrimidine 2′-deoxynucleosides". scheme or table. p. 199 - 207. Retrieved 2010/03/23.
• 2、 Koga,Wilk,Moore,Scremin,Zhou,Beaucage. "Synthesis and physicochemical properties of alternating α,β-oligodeoxyribonucleotides with alternating (3' → 3')- and (5' → 5')-internucleotide phosphodiester linkages". . p. 1520 - 1530. Retrieved 2007/10/02.