N³-pivaloyloxymethyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[N-(2,3-diacetoxypropyl)aminocarbonyl]methyluridine

Base Information

• Chemical Name: N³-pivaloyloxymethyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[N-(2,3-diacetoxypropyl)aminocarbonyl]methyluridine
• CAS No.: 863446-50-8
• Molecular Formula: C₄₅H₅₃N₃O₁₅
• Molecular Weight: 875.927

Synonyms:N³-pivaloyloxymethyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[N-(2,3-diacetoxypropyl)aminocarbonyl]methyluridine

Chemical Property of N³-pivaloyloxymethyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[N-(2,3-diacetoxypropyl)aminocarbonyl]methyluridine

Chemical Property:

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Technology Process of N³-pivaloyloxymethyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[N-(2,3-diacetoxypropyl)aminocarbonyl]methyluridine

There total 7 articles about N³-pivaloyloxymethyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[N-(2,3-diacetoxypropyl)aminocarbonyl]methyluridine 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: 84.3%

4,4'-dimethoxytrityl chloride (40615-36-9) + N3-pivaloyloxymethyl-2'-O-[N-(2,3-diacetoxypropyl)aminocarbonyl]methyluridine (863446-49-5) → N3-pivaloyloxymethyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[N-(2,3-diacetoxypropyl)aminocarbonyl]methyluridine (863446-50-8)

Guidance literature:

With pyridine;

DOI:10.1016/j.bmc.2005.05.024

Reference yield:

N3-pivaloyloxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine (195247-12-2) → N3-pivaloyloxymethyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[N-(2,3-diacetoxypropyl)aminocarbonyl]methyluridine (863446-50-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / tert-butylimino-tri(pyrrolidino)phosphorane / acetonitrile; tetrahydrofuran / 3 h

2: ethanol

3: 87.4 percent / pyridine; 4-(dimethylamino)pyridine / tetrahydrofuran / 5 h / 20 °C

4: 95.3 percent / triethylamine trihydrofluoride / tetrahydrofuran / 1.5 h

5: 84.3 percent / pyridine

With pyridine; dmap; triethylamine trihydrofluoride; tert-butylimino-tri(pyrrolidino)phosphorane; In tetrahydrofuran; ethanol; acetonitrile;

DOI:10.1016/j.bmc.2005.05.024

Reference yield:

2'-O-(2-benzyloxy-2-oxoethyl)-N3-pivaloyloxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine (863446-47-3) → N3-pivaloyloxymethyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[N-(2,3-diacetoxypropyl)aminocarbonyl]methyluridine (863446-50-8)

Guidance literature:

Multi-step reaction with 4 steps

1: ethanol

2: 87.4 percent / pyridine; 4-(dimethylamino)pyridine / tetrahydrofuran / 5 h / 20 °C

3: 95.3 percent / triethylamine trihydrofluoride / tetrahydrofuran / 1.5 h

4: 84.3 percent / pyridine

With pyridine; dmap; triethylamine trihydrofluoride; In tetrahydrofuran; ethanol;

DOI:10.1016/j.bmc.2005.05.024

upstream raw materials:

4,4'-dimethoxytrityl chloride

N³-pivaloyloxymethyl-2'-O-[N-(2,3-diacetoxypropyl)aminocarbonyl]methyluridine

Chloromethyl pivalate

N³-pivaloyloxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine

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