5-[(17β-acetoxy-3-methoxyestra-1,3,5(10)-trien-17α-yl)ethynyl]-7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Base Information

• Chemical Name: 5-[(17β-acetoxy-3-methoxyestra-1,3,5(10)-trien-17α-yl)ethynyl]-7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-7H-pyrrolo[2,3-d]pyrimidin-4-amine
• CAS No.: 259097-19-3
• Molecular Formula: C₅₈H₆₃N₅O₈
• Molecular Weight: 958.167

Synonyms:5-[(17β-acetoxy-3-methoxyestra-1,3,5(10)-trien-17α-yl)ethynyl]-7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Chemical Property of 5-[(17β-acetoxy-3-methoxyestra-1,3,5(10)-trien-17α-yl)ethynyl]-7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Chemical Property:

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Technology Process of 5-[(17β-acetoxy-3-methoxyestra-1,3,5(10)-trien-17α-yl)ethynyl]-7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

There total 4 articles about 5-[(17β-acetoxy-3-methoxyestra-1,3,5(10)-trien-17α-yl)ethynyl]-7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-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:

(8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate (10382-22-6) → 5-[(17β-acetoxy-3-methoxyestra-1,3,5(10)-trien-17α-yl)ethynyl]-7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N4-[(dimethylamino)methylidene]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (259097-19-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 59 percent / CuI; Et₃N; [Pd(PPh₃)4] / dimethylformamide / 3 h / 20 °C

2: 70 percent / methanol / 24 h / 80 °C

3: 68 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:

mestranol (72-33-3) → 5-[(17β-acetoxy-3-methoxyestra-1,3,5(10)-trien-17α-yl)ethynyl]-7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N4-[(dimethylamino)methylidene]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (259097-19-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / pyridine / 12 h / Heating

2: 59 percent / CuI; Et₃N; [Pd(PPh₃)4] / dimethylformamide / 3 h / 20 °C

3: 70 percent / methanol / 24 h / 80 °C

4: 68 percent / pyridine / 1 h / 50 °C

With pyridine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In methanol; N,N-dimethyl-formamide; 1: Acetylation / 2: Substitution / 3: Condensation / 4: 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) → 5-[(17β-acetoxy-3-methoxyestra-1,3,5(10)-trien-17α-yl)ethynyl]-7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N4-[(dimethylamino)methylidene]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (259097-19-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 59 percent / CuI; Et₃N; [Pd(PPh₃)4] / dimethylformamide / 3 h / 20 °C

2: 70 percent / methanol / 24 h / 80 °C

3: 68 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:

(8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate

mestranol

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

5-[2-(17β-acetoxy-3-methoxyestra-1,3,5(10)-trien-17α-yl)ethynyl]-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Downstream raw materials:

5-[(17β-acetoxy-3-methoxyestra-1,3,5(10)-trien-17α-yl)ethynyl]7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 3'-(2-cyanoethyl diisopropylphosphoramidite)

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