2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N₃{tetramethyl 2,2',2'',2'''-[(4-(hex-5-yn-1-yl)pyridine-2,6-diyl)]bis(methylene-nitrilo)}tetrakis(acetato)uridine

Base Information

• Chemical Name: 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N₃{tetramethyl 2,2',2'',2'''-[(4-(hex-5-yn-1-yl)pyridine-2,6-diyl)]bis(methylene-nitrilo)}tetrakis(acetato)uridine
• CAS No.: 358978-73-1
• Molecular Formula: C₅₅H₆₃N₅O₁₅
• Molecular Weight: 1034.13

Synonyms:2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N₃{tetramethyl 2,2',2'',2'''-[(4-(hex-5-yn-1-yl)pyridine-2,6-diyl)]bis(methylene-nitrilo)}tetrakis(acetato)uridine

Chemical Property of 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N₃{tetramethyl 2,2',2'',2'''-[(4-(hex-5-yn-1-yl)pyridine-2,6-diyl)]bis(methylene-nitrilo)}tetrakis(acetato)uridine

Chemical Property:

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Technology Process of 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N₃{tetramethyl 2,2',2'',2'''-[(4-(hex-5-yn-1-yl)pyridine-2,6-diyl)]bis(methylene-nitrilo)}tetrakis(acetato)uridine

There total 3 articles about 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N₃{tetramethyl 2,2',2'',2'''-[(4-(hex-5-yn-1-yl)pyridine-2,6-diyl)]bis(methylene-nitrilo)}tetrakis(acetato)uridine 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: 70.0%

DMT-dU (23669-79-6) + tetramethyl 2,2',2'',2'''-[((6-hydroxy-1-hexyn-2-yl)pyridine-2,6-diyl)bis(methylenenitrilo)]tetrakis(acetate) (358978-71-9) → 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N3{tetramethyl 2,2',2'',2'''-[(4-(hex-5-yn-1-yl)pyridine-2,6-diyl)]bis(methylene-nitrilo)}tetrakis(acetato)uridine (358978-73-1)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/ol016093m

Reference yield:

5-hexyl-1-ol (928-90-5) → 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N3{tetramethyl 2,2',2'',2'''-[(4-(hex-5-yn-1-yl)pyridine-2,6-diyl)]bis(methylene-nitrilo)}tetrakis(acetato)uridine (358978-73-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / CuI; Et₃N / bis(triphenyl-phosphine)palladium(II) chloride / tetrahydrofuran / 7 h / 55 °C

2: 70 percent / PPh₃; DEAD / tetrahydrofuran / 2 h / 20 °C

With copper(l) iodide; triethylamine; triphenylphosphine; diethylazodicarboxylate; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; 2: Mitsunobu reaction;

DOI:10.1021/ol016093m

Reference yield:

tetramethyl 2,2',2'',2'''-[(4-bromopyridine-2,6-diyl)bis(methylenenitrilo)]tetrakis(acetate) → 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N3{tetramethyl 2,2',2'',2'''-[(4-(hex-5-yn-1-yl)pyridine-2,6-diyl)]bis(methylene-nitrilo)}tetrakis(acetato)uridine (358978-73-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / CuI; Et₃N / bis(triphenyl-phosphine)palladium(II) chloride / tetrahydrofuran / 7 h / 55 °C

2: 70 percent / PPh₃; DEAD / tetrahydrofuran / 2 h / 20 °C

With copper(l) iodide; triethylamine; triphenylphosphine; diethylazodicarboxylate; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; 2: Mitsunobu reaction;

DOI:10.1021/ol016093m

upstream raw materials:

DMT-dU

tetramethyl 2,2',2'',2'''-[((6-hydroxy-1-hexyn-2-yl)pyridine-2,6-diyl)bis(methylenenitrilo)]tetrakis(acetate)

5-hexyl-1-ol

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