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

Base Information

• Chemical Name: (E)-N⁶-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanylidene)-5'-deoxyadenosine
• CAS No.: 85681-03-4
• Molecular Formula: C₂₄H₂₃N₅O₆
• Molecular Weight: 477.477

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (E)-N⁶-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanylidene)-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: 68.0%

6-N-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde (43077-06-1) + 3-(triphenylphosphoranyliden)dihydro-2(3H)-furanone (34932-07-5) → (E)-N6-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanylidene)-5'-deoxyadenosine (85681-03-4)

Guidance literature:

In dichloromethane; acetonitrile; benzene; at 60 ℃; for 1h;

DOI:10.1021/jo00160a008

Reference yield:

(E)-N6-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanylidene)-5'-deoxyadenosine (85681-03-4) → 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 (85681-18-1,85681-19-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / H₂ / PtO₂ / ethanol / 50 h / 3102.9 Torr

2: 77 percent / ethane-1,2-diol / 6 h / 110 °C

3: NaOH / ethanol; H₂O / 1 h / 80 °C

4: imidazole / dimethylformamide / 5 h / Ambient temperature

5: 90 percent / NaOH, H₂O / tetrahydrofuran / 2 h / 0 °C

6: potassium tert-butoxide, oxalyl chloride / methanol; benzene / 0.5 h

7: 1.) sodium azide; / 1.) acetone, 0 deg C, 90 min.; 2.) reflux, 4h

8: 62 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.75 h / Ambient temperature

9: CH₂Cl₂; triethylamine / 1 h / Ambient temperature

With 1H-imidazole; sodium hydroxide; sodium azide; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethylene glycol; triethylamine; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00160a008

Reference yield:

(E)-N6-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanylidene)-5'-deoxyadenosine (85681-03-4) → (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 (85681-11-4,85681-12-5,126722-17-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / H₂ / PtO₂ / ethanol / 50 h / 3102.9 Torr

2: 77 percent / ethane-1,2-diol / 6 h / 110 °C

3: NaOH / ethanol; H₂O / 1 h / 80 °C

4: imidazole / dimethylformamide / 5 h / Ambient temperature

5: 90 percent / NaOH, H₂O / tetrahydrofuran / 2 h / 0 °C

6: potassium tert-butoxide, oxalyl chloride / methanol; benzene / 0.5 h

With 1H-imidazole; sodium hydroxide; oxalyl dichloride; potassium tert-butylate; water; hydrogen; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; water; ethylene glycol; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00160a008

upstream raw materials:

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

3-(triphenylphosphoranyliden)dihydro-2(3H)-furanone

Downstream raw materials:

{(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

9-<6-(R,S)-<2-(tert-butyldiphenylsiloxy)ethyl>-2,3-O-isopropylidene-5,6-dideoxy-β-D-ribo-heptofuranosyluronic acid>adenine

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