N⁶-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanyl)-5'-deoxyadenosine

Base Information

• Chemical Name: N⁶-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanyl)-5'-deoxyadenosine
• CAS No.: 85681-04-5
• Molecular Formula: C₂₄H₂₅N₅O₆
• Molecular Weight: 479.492
• Mol file: 85681-04-5.mol

Synonyms:N⁶-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanyl)-5'-deoxyadenosine

Chemical Property of N⁶-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanyl)-5'-deoxyadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁶-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanyl)-5'-deoxyadenosine

There total 1 articles about N⁶-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanyl)-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:

6-N-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde (43077-06-1) → N6-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanyl)-5'-deoxyadenosine (85681-04-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / benzene; acetonitrile; CH₂Cl₂ / 1 h / 60 °C

2: 90 percent / H₂ / PtO₂ / ethanol / 50 h / 3102.9 Torr

With hydrogen; platinum(IV) oxide; In ethanol; dichloromethane; acetonitrile; benzene;

DOI:10.1021/jo00160a008

Reference yield: 74.0%

N6-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanyl)-5'-deoxyadenosine (85681-04-5) → N6-benzoyl-2',3'-isopropylidene-5'-(2-hydroxytetrahydrofuran-3-yl)-5'-deoxyadenosine (126616-46-4)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; for 3h;

DOI:10.1021/jo00297a034

Reference yield:

N6-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanyl)-5'-deoxyadenosine (85681-04-5) → N6-benzoyl-2',3'-isopropylidene-5'-(5-((tert-butyldiphenylsilyl)oxy)-1-phenyl-1-pentyn-3-yl)-5'-deoxyadenosine (126616-54-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / DIBAL / tetrahydrofuran; toluene / 3 h / -78 °C

2: 39 percent / imidazole / dimethylformamide; hexamethylphosphoric acid triamide / 1.33 h / 50 °C

3: 31 percent / potassium tert-butoxide / tetrahydrofuran / -78 °C / a) 15 min b) 5 h

4: 78 percent / CuI, Et₃N / PdCl₂(PPh₃)2 / a) 50 deg C, 3 h b) room temp., overnight

With 1H-imidazole; copper(l) iodide; potassium tert-butylate; diisobutylaluminium hydride; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00297a034

upstream raw materials:

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

Downstream raw materials:

N⁶-benzoyl-2',3'-isopropylidene-5'-(2-hydroxytetrahydrofuran-3-yl)-5'-deoxyadenosine

{(S)-1-[(3aS,4S,6S,6aS)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-3-hydroxy-propyl}-carbamic acid benzyl ester

Methanesulfonic acid (S)-4-[(3aS,4S,6S,6aS)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-benzyloxycarbonylamino-butyl ester

(S)-2-[(3aS,4S,6S,6aS)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-4-(tert-butyl-diphenyl-silanyloxy)-butyryl chloride