2'-O-3'-O,N⁽⁴⁾-Triacetylarabinofuranosylcytidylyl 5'-(2',3'-di-O-isopropylidene-6-methylthiopurine riboside), 5'-(2-chlorophenyl)phosphate

Base Information

• Chemical Name: 2'-O-3'-O,N⁽⁴⁾-Triacetylarabinofuranosylcytidylyl 5'-(2',3'-di-O-isopropylidene-6-methylthiopurine riboside), 5'-(2-chlorophenyl)phosphate
• CAS No.: 91146-91-7
• Molecular Formula: C₃₅H₃₉ClN₇O₁₄PS
• Molecular Weight: 880.226
• Mol file: 91146-91-7.mol

Synonyms:

Chemical Property of 2'-O-3'-O,N⁽⁴⁾-Triacetylarabinofuranosylcytidylyl 5'-(2',3'-di-O-isopropylidene-6-methylthiopurine riboside), 5'-(2-chlorophenyl)phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-O-3'-O,N⁽⁴⁾-Triacetylarabinofuranosylcytidylyl 5'-(2',3'-di-O-isopropylidene-6-methylthiopurine riboside), 5'-(2-chlorophenyl)phosphate

There total 4 articles about 2'-O-3'-O,N⁽⁴⁾-Triacetylarabinofuranosylcytidylyl 5'-(2',3'-di-O-isopropylidene-6-methylthiopurine riboside), 5'-(2-chlorophenyl)phosphate 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: 90.0%

Phosphoric acid 2-chloro-phenyl ester (3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-methylsulfanyl-purin-9-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester; compound with triethyl-amine (91146-90-6) + N4-acetyl-1-<2',3'-di-O-acetyl-β-D-arabinofuranosyl>cytosine (15465-98-2) → 2'-O-3'-O,N(4)-Triacetylarabinofuranosylcytidylyl 5'-(2',3'-di-O-isopropylidene-6-methylthiopurine riboside), 5'-(2-chlorophenyl)phosphate (91146-91-7)

Guidance literature:

With pyridine; 3-nitro-1,2,4-triazole; 2-quinolinesulfonyl chloride; for 20h; Ambient temperature;

DOI:10.1007/BF00758998

Reference yield:

6-methylmercaptopurine riboside (342-69-8) → 2'-O-3'-O,N(4)-Triacetylarabinofuranosylcytidylyl 5'-(2',3'-di-O-isopropylidene-6-methylthiopurine riboside), 5'-(2-chlorophenyl)phosphate (91146-91-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 77.3 percent / 60percent aq. HClO₄ / 2 h / Ambient temperature

3: pyridine / 20 h / Ambient temperature

4: 90 percent / pyridine, 3-nitro-1,2,4-triazole, quinolinesulfonyl chloride / 20 h / Ambient temperature

With pyridine; perchloric acid; 3-nitro-1,2,4-triazole; 2-quinolinesulfonyl chloride;

DOI:10.1007/BF00758998

Reference yield:

O2,O3-isopropylidene-1-(6-methylsulfanyl-purin-9-yl)-β-D-1-deoxy-ribofuranose (42021-78-3) → 2'-O-3'-O,N(4)-Triacetylarabinofuranosylcytidylyl 5'-(2',3'-di-O-isopropylidene-6-methylthiopurine riboside), 5'-(2-chlorophenyl)phosphate (91146-91-7)

Guidance literature:

Multi-step reaction with 3 steps

2: pyridine / 20 h / Ambient temperature

3: 90 percent / pyridine, 3-nitro-1,2,4-triazole, quinolinesulfonyl chloride / 20 h / Ambient temperature

With pyridine; 3-nitro-1,2,4-triazole; 2-quinolinesulfonyl chloride;

DOI:10.1007/BF00758998

upstream raw materials:

Phosphoric acid 2-chloro-phenyl ester (3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-methylsulfanyl-purin-9-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester; compound with triethyl-amine

N⁴-acetyl-1-<2',3'-di-O-acetyl-β-D-arabinofuranosyl>cytosine

6-methylmercaptopurine riboside

2',3'-Di-O-isopropylidene-6-methylthiopurine riboside 5'-(2-chlorophenyl, 2-cyanoethyl)-phosphate

Refernces