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

Base Information

• Chemical Name: 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-6-iodo-N₃-(p-methoxybenzyl)uridine
• CAS No.: 1311164-83-6
• Molecular Formula: C₂₆H₃₇IN₂O₇Si
• Molecular Weight: 644.579

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

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

Chemical Property:

Purity/Quality:

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

There total 3 articles about 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-6-iodo-N₃-(p-methoxybenzyl)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: 43.0%

5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N3-(p-methoxybenzyl)uridine (929902-03-4) → 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-6-iodo-N3-(p-methoxybenzyl)uridine (1311164-83-6)

Guidance literature:

5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N₃-(p-methoxybenzyl)uridine; With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at -78 ℃; for 1h; Inert atmosphere;

With iodine; In tetrahydrofuran; n-heptane; ethylbenzene; at -78 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tet.2011.03.051

Reference yield:

5'-O-(t-butyldimethylsilyl)-2',3'-O-isopropylideneuridine (102147-76-2) → 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-6-iodo-N3-(p-methoxybenzyl)uridine (1311164-83-6)

Guidance literature:

Multi-step reaction with 2 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

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; acetonitrile;

DOI:10.1016/j.tet.2011.03.051

Reference yield:

p-methoxybenzyl chloride (824-94-2) → 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-6-iodo-N3-(p-methoxybenzyl)uridine (1311164-83-6)

Guidance literature:

Multi-step reaction with 2 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

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; acetonitrile;

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-(t-butyldimethylsilyl)-2',3'-O-isopropylideneuridine

p-methoxybenzyl chloride

Downstream raw materials:

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

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

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

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