(E)-N⁶-benzoyl-4',5'-didehydro-5'-chloro-5'-fluoro-2',3'-O-isopropylideneadenosine

Base Information

• Chemical Name: (E)-N⁶-benzoyl-4',5'-didehydro-5'-chloro-5'-fluoro-2',3'-O-isopropylideneadenosine
• CAS No.: 133167-64-3
• Molecular Formula: C₂₀H₁₇ClFN₅O₄
• Molecular Weight: 445.837

Synonyms:(E)-N⁶-benzoyl-4',5'-didehydro-5'-chloro-5'-fluoro-2',3'-O-isopropylideneadenosine

Chemical Property of (E)-N⁶-benzoyl-4',5'-didehydro-5'-chloro-5'-fluoro-2',3'-O-isopropylideneadenosine

Chemical Property:

Purity/Quality:

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Technology Process of (E)-N⁶-benzoyl-4',5'-didehydro-5'-chloro-5'-fluoro-2',3'-O-isopropylideneadenosine

There total 4 articles about (E)-N⁶-benzoyl-4',5'-didehydro-5'-chloro-5'-fluoro-2',3'-O-isopropylideneadenosine 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: 45.0%

N-Benzoyl-N-(9-{(3aR,4R,6S,6aS)-6-[chloro-fluoro-(4-methoxy-benzenesulfinyl)-methyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-yl)-benzamide (133191-04-5) → (E)-N6-benzoyl-4',5'-didehydro-5'-chloro-5'-fluoro-2',3'-O-isopropylideneadenosine (133167-64-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In diethylene glycol dimethyl ether; for 18h; Heating;

DOI:10.1021/jm00106a028

Reference yield:

N-Benzoyl-N-{9-[(3aR,4R,6S,6aS)-6-(4-methoxy-phenylsulfanylmethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-benzamide (133167-55-2) → (E)-N6-benzoyl-4',5'-didehydro-5'-chloro-5'-fluoro-2',3'-O-isopropylideneadenosine (133167-64-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 55 percent / 3-chloroperbenzoic acid / CH₂Cl₂

2: 46 percent / (diethylamido)sulfur triluoride (DAST) / CHCl₃

3: 60 percent / 3-chloroperbenzoic acid / CH₂Cl₂

4: 31 percent / SO₂Cl₂, pyridine / CH₂Cl₂

5: 45 percent / EtN(iPr)2 / bis-(2-methoxy-ethyl) ether / 18 h / Heating

With pyridine; sulfuryl dichloride; (diethylamido)sulfur triluoride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; chloroform; diethylene glycol dimethyl ether;

DOI:10.1021/jm00106a028

Reference yield:

N-Benzoyl-N-{9-[(3aR,4R,6S,6aS)-6-(4-methoxy-benzenesulfinylmethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-benzamide (133167-56-3,133191-03-4) → (E)-N6-benzoyl-4',5'-didehydro-5'-chloro-5'-fluoro-2',3'-O-isopropylideneadenosine (133167-64-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 46 percent / (diethylamido)sulfur triluoride (DAST) / CHCl₃

2: 60 percent / 3-chloroperbenzoic acid / CH₂Cl₂

3: 31 percent / SO₂Cl₂, pyridine / CH₂Cl₂

4: 45 percent / EtN(iPr)2 / bis-(2-methoxy-ethyl) ether / 18 h / Heating

With pyridine; sulfuryl dichloride; (diethylamido)sulfur triluoride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; chloroform; diethylene glycol dimethyl ether;

DOI:10.1021/jm00106a028

upstream raw materials:

N-Benzoyl-N-(9-{(3aR,4R,6S,6aS)-6-[chloro-fluoro-(4-methoxy-benzenesulfinyl)-methyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-yl)-benzamide

N-Benzoyl-N-{9-[(3aR,4R,6S,6aS)-6-(4-methoxy-phenylsulfanylmethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-benzamide

N-Benzoyl-N-{9-[(3aR,4R,6S,6aS)-6-(4-methoxy-benzenesulfinylmethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-benzamide

9-[(3aR,4R,6S,6aS)-6-(4-Methoxy-phenylsulfanylmethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-ylamine

Downstream raw materials:

N-(9-{(2R,3R,4S)-5-[1-Chloro-1-fluoro-meth-(E)-ylidene]-3,4-dihydroxy-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide

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