N4-BENZOYL-2'-O-METHYLCYTIDINE

Base Information

• Chemical Name: N4-BENZOYL-2'-O-METHYLCYTIDINE
• CAS No.: 52571-45-6
• Molecular Formula: C17H19 N3 O6
• Molecular Weight: 361.354
• Mol file: 52571-45-6.mol

Synonyms:N4-Benzoyl-2'-O-methylcytidine;NSC 371910

Chemical Property of N4-BENZOYL-2'-O-METHYLCYTIDINE

Chemical Property:

• Melting Point: 174-175oC
• PKA: 8.59±0.20(Predicted)
• PSA: 122.91000
• Density: 1.49g/cm3
• LogP: -0.16580
• Storage Temp.: 2-8°C

Purity/Quality:

98%, ^*data from raw suppliers

N4-Benzoyl-2'-O-methylcytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N4-Benzoyl-2’-O-methylcytidine is a key building block in the block synthesis strategy of tRNA fragments.

Technology Process of N4-BENZOYL-2'-O-METHYLCYTIDINE

There total 11 articles about N4-BENZOYL-2'-O-METHYLCYTIDINE 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: 80.0%

N4-benzoyl-3',5'-di-O-benzoyl-2'-O-methylcytidine (73793-16-5) → 2'-O-methyl-N4-benzoylcytidine (52571-45-6)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; for 0.2h; Ambient temperature;

DOI:10.1021/jo00341a005

Reference yield: 56.0%

1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N4-benzoylcytosine (69304-43-4) + methyl iodide (74-88-4) → 2'-O-methyl-N4-benzoylcytidine (52571-45-6)

Guidance literature:

With silver(l) oxide; In acetone; at 20 ℃; for 20h;

DOI:10.1007/BF00597663

Reference yield:

1,3,5-tri-O-benzoyl-α-D-ribofuranoside (22224-41-5) → 2'-O-methyl-N4-benzoylcytidine (52571-45-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / BF₃*(C₂H₅)2O / CH₂Cl₂ / 0 °C

2: 1.) HMDS, (NH₄)2SO₄, 2.) SnCl₄ / 1.) reflux, overnight, 2.) dichloroethane, reflux, 60 min

3: 80 percent / NaOCH₃ / tetrahydrofuran; methanol / 0.2 h / Ambient temperature

With ammonium sulfate; boron trifluoride diethyl etherate; sodium methylate; tin(IV) chloride; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00341a005

upstream raw materials:

diazomethane

N₄-benzoylcytidine

benzoic acid anhydride

2'-O-methylcytidine

Downstream raw materials:

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

Refernces

• 1、 Metelev, Valerii G.,Krynetskaya, Natalya F.,Purmal, Andrei A.,Shabarova, Zoya A.,Tocik, Zdenek,et al.. "REGIOSPECIFIC CLEAVAGE OF RNA BY RNASE H FROM E. coli IN THE PRESENCE OF A COMPLEMENTARY OLIGONUCLEOTIDE WITH INSERTED ALTERNATING 2'-O-METHYLCYTIDINE RESIDUES". . p. 2781 - 2786. Retrieved 2007/10/02.
• 2、 Heikkilae, Jarmo,Bjoerkman, Sven,Oeberg, Bo,Chattopadhyaya, Jyoti. "5'-O-Trityl Group Promoted Directive Effect in the Preparation of 2'-O-Methylribonucleosides". . p. 715 - 718. Retrieved 2007/10/02.