(1S,3R,4R,6R,7S)-7-(P-2-cyanoethoxy-N,N-diisopropylaminophosphinyl)oxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(thymin-1-yl)-6-(4-(thymin-1-ylmethyl)-1,2,3-triazol-1-yl)methyl-2,5-dioxabicyclo[2.2.1]heptane

Base Information

• Chemical Name: (1S,3R,4R,6R,7S)-7-(P-2-cyanoethoxy-N,N-diisopropylaminophosphinyl)oxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(thymin-1-yl)-6-(4-(thymin-1-ylmethyl)-1,2,3-triazol-1-yl)methyl-2,5-dioxabicyclo[2.2.1]heptane
• CAS No.: 1278593-97-7
• Molecular Formula: C₅₀H₅₈N₉O₁₁P
• Molecular Weight: 992.038

Synonyms:(1S,3R,4R,6R,7S)-7-(P-2-cyanoethoxy-N,N-diisopropylaminophosphinyl)oxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(thymin-1-yl)-6-(4-(thymin-1-ylmethyl)-1,2,3-triazol-1-yl)methyl-2,5-dioxabicyclo[2.2.1]heptane

Chemical Property of (1S,3R,4R,6R,7S)-7-(P-2-cyanoethoxy-N,N-diisopropylaminophosphinyl)oxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(thymin-1-yl)-6-(4-(thymin-1-ylmethyl)-1,2,3-triazol-1-yl)methyl-2,5-dioxabicyclo[2.2.1]heptane

Chemical Property:

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Technology Process of (1S,3R,4R,6R,7S)-7-(P-2-cyanoethoxy-N,N-diisopropylaminophosphinyl)oxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(thymin-1-yl)-6-(4-(thymin-1-ylmethyl)-1,2,3-triazol-1-yl)methyl-2,5-dioxabicyclo[2.2.1]heptane

There total 5 articles about (1S,3R,4R,6R,7S)-7-(P-2-cyanoethoxy-N,N-diisopropylaminophosphinyl)oxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(thymin-1-yl)-6-(4-(thymin-1-ylmethyl)-1,2,3-triazol-1-yl)methyl-2,5-dioxabicyclo[2.2.1]heptane 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: 41.0%

(1S,3R,4R,6R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-6-(4-(thymin-1-ylmethyl)-1,2,3-triazol-1-yl)methyl-2,5-dioxabicyclo[2.2.1]heptane (1278593-96-6) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → (1S,3R,4R,6R,7S)-7-(P-2-cyanoethoxy-N,N-diisopropylaminophosphinyl)oxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(thymin-1-yl)-6-(4-(thymin-1-ylmethyl)-1,2,3-triazol-1-yl)methyl-2,5-dioxabicyclo[2.2.1]heptane (1278593-97-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1039/c0ob00438c

Reference yield:

(1S,3R,4R,6R,7S)-6-azidomethyl-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (1052725-50-4) → (1S,3R,4R,6R,7S)-7-(P-2-cyanoethoxy-N,N-diisopropylaminophosphinyl)oxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(thymin-1-yl)-6-(4-(thymin-1-ylmethyl)-1,2,3-triazol-1-yl)methyl-2,5-dioxabicyclo[2.2.1]heptane (1278593-97-7)

Guidance literature:

Multi-step reaction with 4 steps

1: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; tert-butyl alcohol / Inert atmosphere; Microwave irradiation

2: palladium on carbon; hydrogen / ethanol / Inert atmosphere

3: pyridine / acetonitrile / 16 h / 20 °C / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

With pyridine; copper(ll) sulfate pentahydrate; palladium on carbon; hydrogen; sodium L-ascorbate; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; water; acetonitrile; tert-butyl alcohol;

DOI:10.1039/c0ob00438c

Reference yield:

(1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-6-((thymin-1-ylmethyl)triazol-1-ylmethyl)-2,5-dioxabicyclo[2.2.1]heptane (1052725-56-0) → (1S,3R,4R,6R,7S)-7-(P-2-cyanoethoxy-N,N-diisopropylaminophosphinyl)oxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(thymin-1-yl)-6-(4-(thymin-1-ylmethyl)-1,2,3-triazol-1-yl)methyl-2,5-dioxabicyclo[2.2.1]heptane (1278593-97-7)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium on carbon; hydrogen / ethanol / Inert atmosphere

2: pyridine / acetonitrile / 16 h / 20 °C / Inert atmosphere

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

With pyridine; palladium on carbon; hydrogen; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; acetonitrile;

DOI:10.1039/c0ob00438c

upstream raw materials:

(1S,3R,4R,6R,7S)-6-azidomethyl-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

(1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-6-((thymin-1-ylmethyl)triazol-1-ylmethyl)-2,5-dioxabicyclo[2.2.1]heptane

(1S,3R,4R,6R,7S)-7-hydroxy-1-hydroxymethyl-3-(thymin-1-yl)-6-((thymin-1-ylmethyl)triazol-1-ylmethyl)-2,5-dioxabicyclo[2.2.1]heptane

(1S,3R,4R,6R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-6-(4-(thymin-1-ylmethyl)-1,2,3-triazol-1-yl)methyl-2,5-dioxabicyclo[2.2.1]heptane

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