7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-5-[5-(trifluoroacetamido)pent-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 3'-(2-cyanoethyl diisopropylphosphoramidite)

Base Information

• Chemical Name: 7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-5-[5-(trifluoroacetamido)pent-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 3'-(2-cyanoethyl diisopropylphosphoramidite)
• CAS No.: 200066-20-2
• Molecular Formula: C₅₁H₆₀F₃N₈O₇P
• Molecular Weight: 985.056

Synonyms:7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-5-[5-(trifluoroacetamido)pent-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 3'-(2-cyanoethyl diisopropylphosphoramidite)

Chemical Property of 7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-5-[5-(trifluoroacetamido)pent-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 3'-(2-cyanoethyl diisopropylphosphoramidite)

Chemical Property:

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Technology Process of 7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-5-[5-(trifluoroacetamido)pent-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 3'-(2-cyanoethyl diisopropylphosphoramidite)

There total 5 articles about 7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-5-[5-(trifluoroacetamido)pent-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 3'-(2-cyanoethyl diisopropylphosphoramidite) 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: 64.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + 7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N4-[(dimethylamino)methylidene]-5-[(5-trifluoroacetamido)pent-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (200066-18-8) → 7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N4-[(dimethylamino)methylidene]-5-[5-(trifluoroacetamido)pent-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 3'-(2-cyanoethyl diisopropylphosphoramidite) (200066-20-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1002/(SICI)1522-2675(19991110)82:11<1878::AID-HLCA1878>3.0.CO;2-W

Reference yield:

N-(4-pentynyl)-trifluoroacetamide (115899-41-7) → 7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N4-[(dimethylamino)methylidene]-5-[5-(trifluoroacetamido)pent-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 3'-(2-cyanoethyl diisopropylphosphoramidite) (200066-20-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 62 percent / CuI; Et₃N; [Pd(PPh₃)4] / dimethylformamide / 4 h / 20 °C

2: 78 percent / methanol / 2 h / 40 °C

3: 60 percent / pyridine / 1 h / 50 °C

4: 64 percent / iPr₂EtN; 59 / tetrahydrofuran / 0.5 h / 20 °C

With pyridine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Substitution / 2: Condensation / 3: Etherification / 4: Substitution;

DOI:10.1002/(SICI)1522-2675(19991110)82:11<1878::AID-HLCA1878>3.0.CO;2-W

Reference yield:

7-deaza-2'-deoxy-7-iodoadenosine (166247-63-8,908130-61-0) → 7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N4-[(dimethylamino)methylidene]-5-[5-(trifluoroacetamido)pent-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 3'-(2-cyanoethyl diisopropylphosphoramidite) (200066-20-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 62 percent / CuI; Et₃N; [Pd(PPh₃)4] / dimethylformamide / 4 h / 20 °C

2: 78 percent / methanol / 2 h / 40 °C

3: 60 percent / pyridine / 1 h / 50 °C

4: 64 percent / iPr₂EtN; 59 / tetrahydrofuran / 0.5 h / 20 °C

With pyridine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Substitution / 2: Condensation / 3: Etherification / 4: Substitution;

DOI:10.1002/(SICI)1522-2675(19991110)82:11<1878::AID-HLCA1878>3.0.CO;2-W

upstream raw materials:

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

7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-5-[(5-trifluoroacetamido)pent-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

N-(4-pentynyl)-trifluoroacetamide

7-deaza-2'-deoxy-7-iodoadenosine

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