N4-BENZOYL-5-METHYLDEOXYCYTIDINE

Base Information

• Chemical Name: N4-BENZOYL-5-METHYLDEOXYCYTIDINE
• CAS No.: 104579-02-4
• Molecular Formula: C₁₇H₁₉N₃O₅
• Molecular Weight: 345.355
• Mol file: 104579-02-4.mol

Synonyms:N4-Benzoyl-2'-deoxy-5-methylcytidine

Chemical Property of N4-BENZOYL-5-METHYLDEOXYCYTIDINE

Chemical Property:

• PKA: 8.69±0.40(Predicted)
• PSA: 113.68000
• Density: 1.46±0.1 g/cm3(Predicted)
• LogP: 0.51770
• Storage Temp.: Store at 0°C

Purity/Quality:

97% ^*data from raw suppliers

N4-BENZOYL-5-METHYLDEOXYCYTIDINE 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N4-BENZOYL-5-METHYLDEOXYCYTIDINE

There total 6 articles about N4-BENZOYL-5-METHYLDEOXYCYTIDINE 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: 73.0%

5-methyl-2'-deoxycytidine hydrochloride (5241-10-1) + benzoyl chloride (98-88-4) → 4-N-benzoyl-5-methyl-2'-deoxycytidine (104579-02-4)

Guidance literature:

In pyridine; 1.) 0 deg C, 10 min; 2.) r.t., 3 h;

DOI:10.1248/cpb.34.51

Reference yield:

Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(4-benzoylamino-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester → 4-N-benzoyl-5-methyl-2'-deoxycytidine (104579-02-4)

Guidance literature:

With sodium hydroxide; In water; at 0 ℃; for 0.0833333h;

DOI:10.1080/15257779908041652

Reference yield:

3',5'-diacetylthymidine (6979-97-1,97834-40-7,142405-86-5) → 4-N-benzoyl-5-methyl-2'-deoxycytidine (104579-02-4)

Guidance literature:

Multi-step reaction with 4 steps

1: POCl₃; triazole / pyridine / 4 h / 20 °C

2: NH₃ / 0.33 h / 0 °C

3: pyridine / 16 h / 20 °C

4: NaOH / H₂O / 0.08 h / 0 °C

With 1,2,3-triazole; sodium hydroxide; ammonia; trichlorophosphate; In pyridine; water; 1: Substitution / 2: Substitution / 3: Substitution / 4: Hydrolysis;

DOI:10.1080/15257779908041652

upstream raw materials:

5-methyl-2'-deoxycytidine hydrochloride

benzoyl chloride

3',5'-diacetylthymidine

5-methyl-1-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)cytidine

Downstream raw materials:

d-<(MeO)2Tr>bzm⁵Cp^.

5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-deoxy-N⁴-benzoyl-5-methylcytidine

Refernces

• 1、 Uesugi,Miyashiro,Tomita,Ikehara. "Synthesis and properties of d(ATACGCGTAT) and its derivatives containing one and two 5-methylcytosine residues. Effect of the methylation on deoxyribonucleic acid conformation". . p. 51 - 60. Retrieved 2007/10/02.