N⁶-(α-imidazolylbenzylidene)-2',3'-isopropylidene-5'-<2--4-azidobutyl>-5'-deoxyadenosine

Base Information

• Chemical Name: N⁶-(α-imidazolylbenzylidene)-2',3'-isopropylidene-5'-<2--4-azidobutyl>-5'-deoxyadenosine
• CAS No.: 166194-01-0
• Molecular Formula: C₃₈H₄₄N₁₄O₅S
• Molecular Weight: 808.924

Synonyms:N⁶-(α-imidazolylbenzylidene)-2',3'-isopropylidene-5'-<2--4-azidobutyl>-5'-deoxyadenosine

Chemical Property of N⁶-(α-imidazolylbenzylidene)-2',3'-isopropylidene-5'-<2--4-azidobutyl>-5'-deoxyadenosine

Chemical Property:

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Technology Process of N⁶-(α-imidazolylbenzylidene)-2',3'-isopropylidene-5'-<2--4-azidobutyl>-5'-deoxyadenosine

There total 7 articles about N⁶-(α-imidazolylbenzylidene)-2',3'-isopropylidene-5'-<2--4-azidobutyl>-5'-deoxyadenosine 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: 38.0%

N6-(α-imidazolylbenzylidene)-2',3'-isopropylidene-5'-<2--4-iodobutyl>-5'-deoxyadenosine (166194-10-1) → N6-(α-imidazolylbenzylidene)-2',3'-isopropylidene-5'-<2--4-azidobutyl>-5'-deoxyadenosine (166194-01-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; for 48h; Ambient temperature;

DOI:10.1021/jm00014a023

Reference yield:

6-N-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde (43077-06-1) → N6-(α-imidazolylbenzylidene)-2',3'-isopropylidene-5'-<2--4-azidobutyl>-5'-deoxyadenosine (166194-01-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) n-BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, from -78 deg C to 0 deg C, 4.25 h

2: 53 percent / H₂ / Pd/C / ethyl acetate / 1034.3 Torr

3: NaCNBH₃, HCl / methanol / Ambient temperature

4: 61 percent / Et₃N / CH₂Cl₂ / Ambient temperature

5: 71 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

6: 76 percent / Ph₃P, I₂ / CH₂Cl₂

7: 38 percent / NaN₃ / dimethylformamide / 48 h / Ambient temperature

With hydrogenchloride; n-butyllithium; sodium azide; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium cyanoborohydride; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00014a023

Reference yield:

N-(9-{(3aR,4R,6R,6aR)-6-[(Z)-5-(tert-Butyl-diphenyl-silanyloxy)-3-oxo-pent-1-enyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-yl)-benzamide (166194-11-2) → N6-(α-imidazolylbenzylidene)-2',3'-isopropylidene-5'-<2--4-azidobutyl>-5'-deoxyadenosine (166194-01-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 53 percent / H₂ / Pd/C / ethyl acetate / 1034.3 Torr

2: NaCNBH₃, HCl / methanol / Ambient temperature

3: 61 percent / Et₃N / CH₂Cl₂ / Ambient temperature

4: 71 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

5: 76 percent / Ph₃P, I₂ / CH₂Cl₂

6: 38 percent / NaN₃ / dimethylformamide / 48 h / Ambient temperature

With hydrogenchloride; sodium azide; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium cyanoborohydride; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00014a023

upstream raw materials:

N⁶-(α-imidazolylbenzylidene)-2',3'-isopropylidene-5'-<2--4-iodobutyl>-5'-deoxyadenosine

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

N-(9-{(3aR,4R,6R,6aR)-6-[(Z)-5-(tert-Butyl-diphenyl-silanyloxy)-3-oxo-pent-1-enyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-yl)-benzamide

N⁶-benzoyl-2',3'-isopropylidene-5'-<2--4-hydroxybutyl>-5'-deoxyadenosine

Downstream raw materials:

N-[3-[(2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-1-(2-azido-ethyl)-propyl]-N-(4-azido-butyl)-4-methyl-benzenesulfonamide

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