(2R,4S,5R)-1-<4-azidotetrahydro-5-<2-(O-phenylphosphono)ethyl>-2-furyl>thymine

Base Information

• Chemical Name: (2R,4S,5R)-1-<4-azidotetrahydro-5-<2-(O-phenylphosphono)ethyl>-2-furyl>thymine
• CAS No.: 142802-33-3
• Molecular Formula: C₁₇H₂₀N₅O₆P
• Molecular Weight: 421.349

Synonyms:(2R,4S,5R)-1-<4-azidotetrahydro-5-<2-(O-phenylphosphono)ethyl>-2-furyl>thymine

Chemical Property of (2R,4S,5R)-1-<4-azidotetrahydro-5-<2-(O-phenylphosphono)ethyl>-2-furyl>thymine

Chemical Property:

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Technology Process of (2R,4S,5R)-1-<4-azidotetrahydro-5-<2-(O-phenylphosphono)ethyl>-2-furyl>thymine

There total 4 articles about (2R,4S,5R)-1-<4-azidotetrahydro-5-<2-(O-phenylphosphono)ethyl>-2-furyl>thymine 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: 79.0%

(2R,4S,5R)-1-<4-azidotetrahydro-5-<2-(di-O-phenylphosphono)ethyl>-2-furyl>thymine (142802-32-2) → (2R,4S,5R)-1-<4-azidotetrahydro-5-<2-(O-phenylphosphono)ethyl>-2-furyl>thymine (142802-33-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; Ambient temperature; pH 11-11.5;

DOI:10.1021/jm00095a014

Reference yield:

diphenyl [(triphenylphosphoranylidene)methyl]phosphonate (22400-41-5) → (2R,4S,5R)-1-<4-azidotetrahydro-5-<2-(O-phenylphosphono)ethyl>-2-furyl>thymine (142802-33-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / tetrahydrofuran / Ambient temperature

2: 70 percent / potassium azodicarboxylate, acetic acid / pyridine / Ambient temperature

3: 79 percent / 1N NaOH / tetrahydrofuran; H₂O / Ambient temperature; pH 11-11.5

With sodium hydroxide; potassium diazodicarboxylate; acetic acid; In tetrahydrofuran; pyridine; water;

DOI:10.1021/jm00095a014

Reference yield:

3'-azido-3'-deoxy0thymidine-5'-aldehyde (116786-62-0) → (2R,4S,5R)-1-<4-azidotetrahydro-5-<2-(O-phenylphosphono)ethyl>-2-furyl>thymine (142802-33-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / tetrahydrofuran / Ambient temperature

2: 70 percent / potassium azodicarboxylate, acetic acid / pyridine / Ambient temperature

3: 79 percent / 1N NaOH / tetrahydrofuran; H₂O / Ambient temperature; pH 11-11.5

With sodium hydroxide; potassium diazodicarboxylate; acetic acid; In tetrahydrofuran; pyridine; water;

DOI:10.1021/jm00095a014

upstream raw materials:

(2R,4S,5R)-1-<4-azidotetrahydro-5-<2-(di-O-phenylphosphono)ethyl>-2-furyl>thymine

diphenyl [(triphenylphosphoranylidene)methyl]phosphonate

3'-azido-3'-deoxy0thymidine-5'-aldehyde

(E,2R,4S,5R)-1-<4-azidotetrahydro-5-<2-(di-O-phenylphosphono)vinyl>-2-furyl>thymine

Downstream raw materials:

6'-<(3'-azido-2',3',5',6'-tetradeoxy-β-D-ribo-hexofuranosyl)-1-thymine>-phosphonic acid

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