{(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

Base Information

• Chemical Name: {(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
• CAS No.: 85681-15-8
• Molecular Formula: C₂₄H₃₀N₆O₆
• Molecular Weight: 498.539

Synonyms:

Chemical Property of {(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(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

There total 9 articles about {(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 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: 62.0%

[(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-(tert-butyl-diphenyl-silanyloxy)-propyl]-carbamic acid benzyl ester (85681-13-6,85681-14-7) → {(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 (85681-15-8,85701-32-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.75h; Ambient temperature;

DOI:10.1021/jo00160a008

Reference yield:

6-N-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde (43077-06-1) → {(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 (85681-15-8,85701-32-2)

Guidance literature:

Multi-step reaction with 9 steps

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

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

3: 77 percent / ethane-1,2-diol / 6 h / 110 °C

4: NaOH / ethanol; H₂O / 1 h / 80 °C

5: imidazole / dimethylformamide / 5 h / Ambient temperature

6: 90 percent / NaOH, H₂O / tetrahydrofuran / 2 h / 0 °C

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

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

9: 62 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.75 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; N,N-dimethyl-formamide; acetonitrile; 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)-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 (85681-15-8,85701-32-2)

Guidance literature:

Multi-step reaction with 8 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

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

DOI:10.1021/jo00160a008

upstream 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-(tert-butyl-diphenyl-silanyloxy)-propyl]-carbamic acid benzyl ester

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

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

2',3'-O-Isopropylidene-5'-C-(2-oxotetrahydro-3-furanyl)-5'-deoxyadenosine

Downstream raw materials:

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

2-{(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}-malonic acid dibenzyl ester

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