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

Base Information

• Chemical Name: 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N³-(p-methoxybenzyl)-6-cyanouridine
• CAS No.: 1429644-28-9
• Molecular Formula: C₂₇H₃₇N₃O₇Si
• Molecular Weight: 543.692

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

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

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

There total 2 articles about 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N³-(p-methoxybenzyl)-6-cyanouridine 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: 47.0%

sodium cyanide (773837-37-9) + 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N3-(p-methoxybenzyl)-5-bromouridine (1429644-26-7) → 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N3-(p-methoxybenzyl)-6-cyanouridine (1429644-28-9)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 2.5h;

DOI:10.1021/jo400364p

Reference yield:

5-bromo-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylidene uridine (869880-87-5) + p-methoxybenzyl chloride (824-94-2) → 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N3-(p-methoxybenzyl)-6-cyanouridine (1429644-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 3 h / 60 °C

2: N,N-dimethyl-formamide / 2.5 h / 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo400364p

Reference yield: 62.0%

5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N3-(p-methoxybenzyl)-6-cyanouridine (1429644-28-9) + ethylmagnesium bromide (925-90-6) → 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N3-(p-methoxybenzyl)-6-ethyluridine (1429644-30-3)

Guidance literature:

With zinc(II) chloride; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; for 3h;

DOI:10.1021/jo400364p

upstream raw materials:

5-bromo-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylidene uridine

p-methoxybenzyl chloride

sodium cyanide

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

Downstream raw materials:

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

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