(E)-N⁶-Benzoyl-9--2,3-O-isopropylidene-β-D-ribo-hept-5-eno-furanosyluronate>adenine

Base Information

• Chemical Name: (E)-N⁶-Benzoyl-9--2,3-O-isopropylidene-β-D-ribo-hept-5-eno-furanosyluronate>adenine
• CAS No.: 85681-01-2
• Molecular Formula: C₂₉H₃₃N₅O₈
• Molecular Weight: 579.61

Synonyms:(E)-N⁶-Benzoyl-9--2,3-O-isopropylidene-β-D-ribo-hept-5-eno-furanosyluronate>adenine

Chemical Property of (E)-N⁶-Benzoyl-9--2,3-O-isopropylidene-β-D-ribo-hept-5-eno-furanosyluronate>adenine

Chemical Property:

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Technology Process of (E)-N⁶-Benzoyl-9--2,3-O-isopropylidene-β-D-ribo-hept-5-eno-furanosyluronate>adenine

There total 6 articles about (E)-N⁶-Benzoyl-9--2,3-O-isopropylidene-β-D-ribo-hept-5-eno-furanosyluronate>adenine 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: 90.0%

6-N-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde (43077-06-1) + <1-(Ethoxycarbonyl)-4,4-(ethylenedioxy)butyl>triphenylphosphonium Iodide (85680-99-5) → (E)-N6-Benzoyl-9--2,3-O-isopropylidene-β-D-ribo-hept-5-eno-furanosyluronate>adenine (85681-01-2)

Guidance literature:

With potassium tert-butylate; In dichloromethane; acetonitrile; benzene; at 40 ℃; for 1h;

DOI:10.1021/jo00160a008

Reference yield: 69.0%

6-N-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde (43077-06-1) + 4-[1,3]Dioxolan-2-yl-2-(triphenyl-λ5-phosphanylidene)-butyric acid ethyl ester (85681-00-1) → (E)-N6-Benzoyl-9--2,3-O-isopropylidene-β-D-ribo-hept-5-eno-furanosyluronate>adenine (85681-01-2)

Guidance literature:

In acetonitrile; for 0.25h; Ambient temperature;

DOI:10.1021/jo00160a008

Reference yield:

1,3-Dioxolan-2-buttersaeure-ethylester (38049-07-9) → (E)-N6-Benzoyl-9--2,3-O-isopropylidene-β-D-ribo-hept-5-eno-furanosyluronate>adenine (85681-01-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / cyclohexylisopropylamine, n-butyllithium, iodine / tetrahydrofuran / 0.25 h / -78 °C

2: 59 percent / tetrahydrothiophene 1,1-dioxide / 4 h / 60 °C

3: 90 percent / potassium tert-butoxide / CH₂Cl₂; acetonitrile; benzene / 1 h / 40 °C

With n-butyllithium; N-cyclohexylisopropylamine; potassium tert-butylate; iodine; In tetrahydrofuran; sulfolane; dichloromethane; acetonitrile; benzene;

DOI:10.1021/jo00160a008

upstream raw materials:

6-N-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde

4-[1,3]Dioxolan-2-yl-2-(triphenyl-λ⁵-phosphanylidene)-butyric acid ethyl ester

<1-(Ethoxycarbonyl)-4,4-(ethylenedioxy)butyl>triphenylphosphonium Iodide

Ethyl 2-ethoxycarbonyl-4-(1',3'-dioxolan-2'-yl)butanoate

Downstream raw materials:

(Z,E)-N⁶-Benzoyl-9--β-D-glycero-hepta-3,5-dienofuranosyluronate>adenine

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