Cytidine, 2'-deoxy-, 3',5'-dibenzoate

Base Information

• Chemical Name: Cytidine, 2'-deoxy-, 3',5'-dibenzoate
• CAS No.: 20963-97-7
• Molecular Formula: C23H21N3O6
• Molecular Weight: 435.436
• Mol file: 20963-97-7.mol

Synonyms:O3',O5'-dibenzoyl-2'-deoxy-cytidine;3',5'-O-O-Dibenzoyldeoxycytidine;3',5'-Di-O-benzoyl-desoxycytidin;

Chemical Property of Cytidine, 2'-deoxy-, 3',5'-dibenzoate

Chemical Property:

• Melting Point: 202-205 °C
• Boiling Point: 614.9±65.0 °C(Predicted)
• PSA: 122.74000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: 2.77680

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cytidine, 2'-deoxy-, 3',5'-dibenzoate

There total 6 articles about Cytidine, 2'-deoxy-, 3',5'-dibenzoate 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: 93.6%

N4-benzoyl-1-(3',5'-di-O-benzoyl-2'-deoxy-β-D-ribofuranosyl)-cytosine (31501-22-1) → 3',5'-di-O-benzoyl-2'-deoxycytidine (20963-97-7)

Guidance literature:

With zinc dibromide; In methanol; chloroform; for 16h; Ambient temperature;

DOI:10.1016/S0040-4039(01)82014-1

Reference yield: 90.0%

2,4-O,N-bis(trimethylsilyl)cytosine (18037-10-0) + C23H29N2O7P (175024-33-6) → C23H21N3O6 (20963-97-7,130703-11-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 0.5h;

DOI:10.3987/com-95-s71

Reference yield: 77.0%

1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-D-erythro-pentafuranose (51255-12-0,2155800-38-5) + bis(trimethylsilyl)cytosine (67014-25-9) → C23H21N3O6 (20963-97-7,130703-11-6)

Guidance literature:

With dibenzo-18-crown-6; potassium iodide; In toluene; acetonitrile; Heating;

DOI:10.1016/S0040-4039(00)97641-X

upstream raw materials:

N⁴-benzoyl-1-(3',5'-di-O-benzoyl-2'-deoxy-β-D-ribofuranosyl)-cytosine

2,4-O,N-bis(trimethylsilyl)cytosine

C₂₃H₂₉N₂O₇P

benzoyl cyanide

Downstream raw materials:

2'-Deoxycytidine

α-2'-deoxycytidine

Refernces

• 1、 Prasad, Ashok K.,Kumar, Vineet,Maity, Jyotirmoy,Wang, Zhiwei,Ravikumar, Vasulinga T.,Sanghvi, Yogesh S.,Parmar, Virinder S.. "Benzoyl cyanide: A mild and efficient reagent for benzoylation of nucleosides". . p. 935 - 945. Retrieved 2007/10/03.
• 2、 Iimori, Takamasa,Kobayashi, Hiroshi,Hashimoto, Shun-Ichi,Ikegami, Shiro. "A mild and rapid glycosylation reaction between pyrimidine bases and 2-deoxyribofuranosyl N,N,N',N'-tetramethylphosphoroamidates". . p. 485 - 488. Retrieved 2007/10/03.