5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N₃-(p-methoxybenzyl)-6-(p-nitrophenyl)uridine

Base Information

• Chemical Name: 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N₃-(p-methoxybenzyl)-6-(p-nitrophenyl)uridine
• CAS No.: 1311164-90-5
• Molecular Formula: C₃₂H₄₁N₃O₉Si
• Molecular Weight: 639.778

Synonyms:5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N₃-(p-methoxybenzyl)-6-(p-nitrophenyl)uridine

Chemical Property of 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N₃-(p-methoxybenzyl)-6-(p-nitrophenyl)uridine

Chemical Property:

Purity/Quality:

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Technology Process of 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N₃-(p-methoxybenzyl)-6-(p-nitrophenyl)uridine

There total 3 articles about 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N₃-(p-methoxybenzyl)-6-(p-nitrophenyl)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: 98.0%

5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-6-iodo-N3-(p-methoxybenzyl)uridine (1311164-83-6) + 4-nitrophenylboronic acid (24067-17-2) → 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N3-(p-methoxybenzyl)-6-(p-nitrophenyl)uridine (1311164-90-5)

Guidance literature:

With palladium diacetate; sodium carbonate; triphenylphosphine; In 1,2-dimethoxyethane; water; for 16h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2011.03.051

Reference yield:

p-methoxybenzyl chloride (824-94-2) → 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N3-(p-methoxybenzyl)-6-(p-nitrophenyl)uridine (1311164-90-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 70 °C

2.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 1 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 °C / Inert atmosphere

3.1: palladium diacetate; sodium carbonate; triphenylphosphine / 1,2-dimethoxyethane; water / 16 h / Inert atmosphere; Reflux

With palladium diacetate; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; n-heptane; ethylbenzene; water; acetonitrile; 3.1: Suzuki-Miyaura coupling;

DOI:10.1016/j.tet.2011.03.051

Reference yield:

5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N3-(p-methoxybenzyl)uridine (929902-03-4) → 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N3-(p-methoxybenzyl)-6-(p-nitrophenyl)uridine (1311164-90-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 1 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 °C / Inert atmosphere

2.1: palladium diacetate; sodium carbonate; triphenylphosphine / 1,2-dimethoxyethane; water / 16 h / Inert atmosphere; Reflux

With palladium diacetate; sodium carbonate; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; n-heptane; ethylbenzene; water; 2.1: Suzuki-Miyaura coupling;

DOI:10.1016/j.tet.2011.03.051

upstream raw materials:

5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N₃-(p-methoxybenzyl)uridine

5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-6-iodo-N₃-(p-methoxybenzyl)uridine

4-nitrophenylboronic acid

p-methoxybenzyl chloride

Downstream raw materials:

6-(p-nitrophenyl)uridine

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