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

Base Information

• Chemical Name: 7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-5-[(3-trifluoroacetamido)prop-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine
• CAS No.: 200066-17-7
• Molecular Formula: C₄₀H₃₉F₃N₆O₆
• Molecular Weight: 756.781

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

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

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

There total 4 articles about 7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-5-[(3-trifluoroacetamido)prop-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 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: 62.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 7-(2-deoxy-β-D-erythro-pentofuranosyl)-N4-[(dimethylamino)methylidene]-5-[3-(trifluoroacetamido)prop-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (259097-09-1) → 7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N4-[(dimethylamino)methylidene]-5-[(3-trifluoroacetamido)prop-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (200066-17-7)

Guidance literature:

With pyridine; at 50 ℃; for 1h;

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

Reference yield:

trifluoroacetyl-propargyl amine (14719-21-2) → 7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N4-[(dimethylamino)methylidene]-5-[(3-trifluoroacetamido)prop-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (200066-17-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 51 percent / CuI; Et₃N; [Pd(PPh₃)4] / dimethylformamide / 3 h / 20 °C

2: 80 percent / methanol / 2 h / 40 °C

3: 62 percent / pyridine / 1 h / 50 °C

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

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-[(3-trifluoroacetamido)prop-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (200066-17-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 51 percent / CuI; Et₃N; [Pd(PPh₃)4] / dimethylformamide / 3 h / 20 °C

2: 80 percent / methanol / 2 h / 40 °C

3: 62 percent / pyridine / 1 h / 50 °C

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

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

upstream raw materials:

4,4'-dimethoxytrityl chloride

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

trifluoroacetyl-propargyl amine

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

Downstream raw materials:

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

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