5'-O-dimethoxytrityl-N³-pivaloyloxymethylthymidine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Base Information

• Chemical Name: 5'-O-dimethoxytrityl-N³-pivaloyloxymethylthymidine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
• CAS No.: 913697-73-1
• Molecular Formula: C₄₆H₅₉N₄O₁₀P
• Molecular Weight: 858.969

Synonyms:5'-O-dimethoxytrityl-N³-pivaloyloxymethylthymidine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Chemical Property of 5'-O-dimethoxytrityl-N³-pivaloyloxymethylthymidine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Chemical Property:

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Technology Process of 5'-O-dimethoxytrityl-N³-pivaloyloxymethylthymidine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

There total 3 articles about 5'-O-dimethoxytrityl-N³-pivaloyloxymethylthymidine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite 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: 86.0%

5'-O-(4-4'-dimethoxytrityl)-N3-pivaloyloxymethylthymidine + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 5'-O-dimethoxytrityl-N3-pivaloyloxymethylthymidine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite (913697-73-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.0075h;

DOI:10.1021/op060133q

Reference yield:

5'-O-(4-4'-dimethoxytrityl)-3'-O-levulinoyl-N3-pivaloyloxymethylthymidine (196200-60-9) → 5'-O-dimethoxytrityl-N3-pivaloyloxymethylthymidine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite (913697-73-1)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid; hydrazine hydrate / pyridine

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.01 h

With hydrazine hydrate; acetic acid; N-ethyl-N,N-diisopropylamine; In pyridine; dichloromethane;

DOI:10.1021/op060133q

Reference yield:

5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2) → 5'-O-dimethoxytrityl-N3-pivaloyloxymethylthymidine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite (913697-73-1)

Guidance literature:

Multi-step reaction with 4 steps

1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,4-dioxane / 2.5 h

2: potassium carbonate / N,N-dimethyl-formamide

3: acetic acid; hydrazine hydrate / pyridine

4: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.01 h

With dmap; potassium carbonate; hydrazine hydrate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; pyridine; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/op060133q

upstream raw materials:

5'-O-(4-4'-dimethoxytrityl)-3'-O-levulinoyl-N³-pivaloyloxymethylthymidine

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

5'-O-(4-4'-dimethoxytrityl)thymidine

Downstream raw materials:

C₄₀H₄₆N₃O₁₁P

C₆₈H₈₄N₅O₁₈P

C₄₀H₄₆N₃O₁₁PS

C₆₈H₈₄N₅O₁₈PS

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