7-(2',3'-O-Isopropylidene-5'-O-trityl-β-D-ribofuranosyl)-4-thioxo-3H,5H-pyrrolo<3,2-d>pyrimidine

Base Information

• Chemical Name: 7-(2',3'-O-Isopropylidene-5'-O-trityl-β-D-ribofuranosyl)-4-thioxo-3H,5H-pyrrolo<3,2-d>pyrimidine
• CAS No.: 84649-19-4
• Molecular Formula: C₃₃H₃₁N₃O₄S
• Molecular Weight: 565.693

Synonyms:7-(2',3'-O-Isopropylidene-5'-O-trityl-β-D-ribofuranosyl)-4-thioxo-3H,5H-pyrrolo<3,2-d>pyrimidine

Chemical Property of 7-(2',3'-O-Isopropylidene-5'-O-trityl-β-D-ribofuranosyl)-4-thioxo-3H,5H-pyrrolo<3,2-d>pyrimidine

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Technology Process of 7-(2',3'-O-Isopropylidene-5'-O-trityl-β-D-ribofuranosyl)-4-thioxo-3H,5H-pyrrolo<3,2-d>pyrimidine

There total 2 articles about 7-(2',3'-O-Isopropylidene-5'-O-trityl-β-D-ribofuranosyl)-4-thioxo-3H,5H-pyrrolo<3,2-d>pyrimidine 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: 82.0%

3-amino-4-(2',3'-di-O-isopropylidene-5'-O-trityl-β-D-ribofuranosyl)-2-thiocarboxamido-1H-pyrrole (83060-69-9) + orthoformic acid triethyl ester (122-51-0) → 7-(2',3'-O-Isopropylidene-5'-O-trityl-β-D-ribofuranosyl)-4-thioxo-3H,5H-pyrrolo<3,2-d>pyrimidine (84649-19-4)

Guidance literature:

at 90 ℃; for 5h;

DOI:10.1021/jo00154a005

Reference yield:

3-Amino-4-((3aS,4S,6R,6aR)-2,2-dimethyl-6-trityloxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrrole-2-carbonitrile (77691-00-0) → 7-(2',3'-O-Isopropylidene-5'-O-trityl-β-D-ribofuranosyl)-4-thioxo-3H,5H-pyrrolo<3,2-d>pyrimidine (84649-19-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / H₂S, Et₃N / pyridine / 24 h / 60 °C

2: 82 percent / 5 h / 90 °C

With hydrogen sulfide; triethylamine; In pyridine;

DOI:10.1021/jo00154a005

Reference yield: 91.0%

7-(2',3'-O-Isopropylidene-5'-O-trityl-β-D-ribofuranosyl)-4-thioxo-3H,5H-pyrrolo<3,2-d>pyrimidine (84649-19-4) + methyl iodide (74-88-4) → 7-(2',3'-O-Isopropylidene-5'-O-trityl-β-D-ribofuranosyl)-4-(methylthio)-5H-pyrrolo<3,2-d>pyrimidine (84649-20-7)

Guidance literature:

With potassium carbonate; In methanol; for 4h; Ambient temperature;

DOI:10.1021/jo00154a005

upstream raw materials:

3-amino-4-(2',3'-di-O-isopropylidene-5'-O-trityl-β-D-ribofuranosyl)-2-thiocarboxamido-1H-pyrrole

orthoformic acid triethyl ester

3-Amino-4-((3aS,4S,6R,6aR)-2,2-dimethyl-6-trityloxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrrole-2-carbonitrile

Downstream raw materials:

7-(2',3'-O-Isopropylidene-5'-O-trityl-β-D-ribofuranosyl)-4-(methylthio)-5H-pyrrolo<3,2-d>pyrimidine

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