N⁶-benzoyl-2',3'-isopropylidene-5'-<2-butyl>-N-(tolylsulfonyl)amino>-4-<(tert-butyldiphenylsilyl)oxy>butyl>-5'-deoxyadenosine

Base Information

• Chemical Name: N⁶-benzoyl-2',3'-isopropylidene-5'-<2-butyl>-N-(tolylsulfonyl)amino>-4-<(tert-butyldiphenylsilyl)oxy>butyl>-5'-deoxyadenosine
• CAS No.: 166194-09-8
• Molecular Formula: C₆₇H₈₀N₆O₈SSi₂
• Molecular Weight: 1185.64

Synonyms:N⁶-benzoyl-2',3'-isopropylidene-5'-<2-butyl>-N-(tolylsulfonyl)amino>-4-<(tert-butyldiphenylsilyl)oxy>butyl>-5'-deoxyadenosine

Chemical Property of N⁶-benzoyl-2',3'-isopropylidene-5'-<2-butyl>-N-(tolylsulfonyl)amino>-4-<(tert-butyldiphenylsilyl)oxy>butyl>-5'-deoxyadenosine

Chemical Property:

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Technology Process of N⁶-benzoyl-2',3'-isopropylidene-5'-<2-butyl>-N-(tolylsulfonyl)amino>-4-<(tert-butyldiphenylsilyl)oxy>butyl>-5'-deoxyadenosine

There total 9 articles about N⁶-benzoyl-2',3'-isopropylidene-5'-<2-butyl>-N-(tolylsulfonyl)amino>-4-<(tert-butyldiphenylsilyl)oxy>butyl>-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: 61.0%

p-toluenesulfonyl chloride (98-59-9) + N6-benzoyl-2',3'-isopropylidene-5'-<2-<<4-<(tert-butyldiphenylsilyl)oxy>butyl>amino>-4-<(tert-butyldiphenylsilyl)oxy>butyl>-5'-deoxyadenosine (166193-99-3) → N6-benzoyl-2',3'-isopropylidene-5'-<2-butyl>-N-(tolylsulfonyl)amino>-4-<(tert-butyldiphenylsilyl)oxy>butyl>-5'-deoxyadenosine (166194-09-8)

Guidance literature:

With triethylamine; In dichloromethane; Ambient temperature;

DOI:10.1021/jm00014a023

Reference yield:

6-N-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde (43077-06-1) → N6-benzoyl-2',3'-isopropylidene-5'-<2-butyl>-N-(tolylsulfonyl)amino>-4-<(tert-butyldiphenylsilyl)oxy>butyl>-5'-deoxyadenosine (166194-09-8)

Guidance literature:

Multi-step reaction with 4 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

With hydrogenchloride; n-butyllithium; hydrogen; sodium cyanoborohydride; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;

DOI:10.1021/jm00014a023

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → N6-benzoyl-2',3'-isopropylidene-5'-<2-butyl>-N-(tolylsulfonyl)amino>-4-<(tert-butyldiphenylsilyl)oxy>butyl>-5'-deoxyadenosine (166194-09-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 50 percent / imidazole / dimethylformamide / Ambient temperature

2: 1.) n-BuLi / 1.) THF, -78 deg C, 75 min, 2.) THF, from -78 deg C to RT, 2 h 20 min

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

4: 53 percent / H₂ / Pd/C / ethyl acetate / 1034.3 Torr

5: NaCNBH₃, HCl / methanol / Ambient temperature

6: 61 percent / Et₃N / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; hydrogenchloride; n-butyllithium; hydrogen; sodium cyanoborohydride; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00014a023

upstream raw materials:

p-toluenesulfonyl chloride

N⁶-benzoyl-2',3'-isopropylidene-5'-<2-<<4-<(tert-butyldiphenylsilyl)oxy>butyl>amino>-4-<(tert-butyldiphenylsilyl)oxy>butyl>-5'-deoxyadenosine

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

tert-butylchlorodiphenylsilane

Downstream raw materials:

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

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

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

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

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