2'-DEOXY-L-CYTIDINE

Base Information

• Chemical Name: 2'-DEOXY-L-CYTIDINE
• CAS No.: 40093-94-5
• Molecular Formula: C9H13 N3 O4
• Molecular Weight: 227.2172
• Mol file: 40093-94-5.mol

Synonyms:2'-Deoxy-L-cytidine;Epcitabine; NV 02C; Torcitabine

Chemical Property of 2'-DEOXY-L-CYTIDINE

Chemical Property:

• Vapor Pressure: 5.47E-12mmHg at 25°C
• Boiling Point: 497.6 °C at 760 mmHg
• PKA: 14.03±0.60(Predicted)
• Flash Point: 254.8 °C
• PSA: 110.60000
• Density: 1.73 g/cm³
• LogP: -0.95260

Purity/Quality:

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

2''-Deoxy-L-cytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Torcitabine (b-L-2u-deoxycytidine) (L-dC) is the b-L-enantiomer of the natural nucleoside D-cytidine. The drug is currently under development by Idenix as an antiviral agent for the treatment of chronic hepatitis B virus infection. Torcitabine has poor oral bioavailability, but its 3u,5u-divaline ester (val-L-dC) and the 3u-monovaline ester, valtorcitabine dihydrochloride, have excellent oral bioavailability and consequently the torcitabine prodrug, valtorcitabine, has replaced torcitabine in clinical development.
• Uses: Torcitabine and its prodrug, valtorcitabine, are investigational drugs being developed solely for the treatment of chronic HBV infection. Torcitabine itself has undergone preliminary phase I/II clinical trials in HBeAg-positive patients, initially as the 3u,5u-divalyl prodrug in escalating doses of 50, 100, 200, and 400 mg/day, but later as the more stable monovaline ester form, valtorcitabine dihydrochloride, and administered to four cohorts in doses of 300, 600, 900, and 1200 mg/ day for 28 days.

Technology Process of 2'-DEOXY-L-CYTIDINE

There total 6 articles about 2'-DEOXY-L-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:

2'-Deoxycytidine (951-77-9) → 2'-deoxycytidine radical cation (951-77-9,4251-19-8,4449-40-5,7060-91-5,40093-94-5,41545-93-1,41545-94-2,64727-75-9,109430-56-0)

Guidance literature:

With sodium chloride; In water; at 20 ℃; Quantum yield; Irradiation;

Reference yield:

C23H21N3O6 (219642-23-6) → L-Deoxycytidine (40093-94-5)

Guidance literature:

With ammonium hydroxide; In 1,4-dioxane; at 55 ℃; for 12h;

DOI:10.1080/07328319808004314

Reference yield:

3',5'-dibenzoyl-2'-deoxy-β-L-uridine (31615-99-3) → L-Deoxycytidine (40093-94-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / 4-chlorophenyl dichlorophosphate / pyridine / 72 h / Ambient temperature

2: 60 percent / aq. NH₃ / dioxane / 1 h / Ambient temperature

3: 0.4 g / conc. aq. NH₃ / dioxane / 12 h / 55 °C

With ammonium hydroxide; 4-chlorophenylphosphorodichloridate; In 1,4-dioxane; pyridine;

DOI:10.1080/07328319808004314

upstream raw materials:

C₂₃H₂₁N₃O₆

C₂₄H₂₀N₆O₆

3',5'-dibenzoyl-2'-deoxy-β-L-uridine

2'-Deoxycytidine

Downstream raw materials:

5'-O-(dimethoxytrityl)-4-N-benzoyl-2'-deoxy-L-cytidine

2'-Deoxycytidine

Refernces

• 1、 Candeias,Steenken. "Ionization of purine nucleosides and nucleotides and their components by 193-nm laser photolysis in aqueous solution: Model studies for oxidative damage of DNA 1". . p. 699 - 704. Retrieved 2007/10/02.