2'-CHLORO-2'-DEOXYCYTIDINE

Base Information

• Chemical Name: 2'-CHLORO-2'-DEOXYCYTIDINE
• CAS No.: 10212-19-8
• Molecular Formula: C₉H₁₂ClN₃O₄
• Molecular Weight: 261.665
• Mol file: 10212-19-8.mol

Synonyms:2-Chloro-2'-deoxycytidine;2'-Deoxy-2'-chlorocytidine;

Chemical Property of 2'-CHLORO-2'-DEOXYCYTIDINE

Chemical Property:

• Boiling Point: 551.253 °C at 760 mmHg
• PKA: 13.00±0.70(Predicted)
• Flash Point: 287.188 °C
• PSA: 110.60000
• Density: 1.863 g/cm³
• LogP: -0.73530

Purity/Quality:

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

2''-Chloro-2''-deoxycytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2''-Chloro-2''-deoxycytidine is a nucleoside derivative.

Technology Process of 2'-CHLORO-2'-DEOXYCYTIDINE

There total 6 articles about 2'-CHLORO-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:

4-Amino-1-((2R,3R,3aR,9aR)-3-chloro-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidin-2-one → 2'-chloro-2'-deoxycytidine (10212-19-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.0833333h;

DOI:10.1002/anie.200353575

Reference yield:

1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]cytosine (75331-99-6) → 2'-chloro-2'-deoxycytidine (10212-19-8)

Guidance literature:

Multi-step reaction with 5 steps

1: dimethylformamide / 2 h

2: 76 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / 0 °C

3: 40 percent / LiCl / dimethylformamide / 1 h / 80 °C

4: aq. NH₄OH; MeNH₂ / 0.17 h / 65 °C

5: 60 mg / tetrabutylammonium fluoride hydrate / tetrahydrofuran / 0.08 h / 20 °C

With dmap; ammonium hydroxide; tetrabutyl ammonium fluoride; methylamine; lithium chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200353575

Reference yield:

N4-acetyl-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]cytosine (161601-95-2) → 2'-chloro-2'-deoxycytidine (10212-19-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: 40 percent / LiCl / dimethylformamide / 1 h / 80 °C

3: aq. NH₄OH; MeNH₂ / 0.17 h / 65 °C

4: 60 mg / tetrabutylammonium fluoride hydrate / tetrahydrofuran / 0.08 h / 20 °C

With dmap; ammonium hydroxide; tetrabutyl ammonium fluoride; methylamine; lithium chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200353575

upstream raw materials:

1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]cytosine

N⁴-acetyl-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]cytosine

N⁴-acetyl-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(trifluoromethanesulfonyl)-β-D-arabinofuranosyl]cytosine

N⁴-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-chloro-2'-deoxycytidine

Refernces

• 1、 Schwans, Jason P.,Li, Nan-Sheng,Piccirilli, Joseph A.. "A packing-density metric for exploring the interior of folded RNA molecules". . p. 3033 - 3037. Retrieved 2004.