4(S)-<4-amino-2-oxo-1(2H)-pyrimidinyl>-2(S)-(O-benzoylmethyl)tetrahydrofuran

Base Information

• Chemical Name: 4(S)-<4-amino-2-oxo-1(2H)-pyrimidinyl>-2(S)-(O-benzoylmethyl)tetrahydrofuran
• CAS No.: 151223-92-6
• Molecular Formula: C₁₆H₁₇N₃O₄
• Molecular Weight: 315.329
• Mol file: 151223-92-6.mol

Synonyms:4(S)-<4-amino-2-oxo-1(2H)-pyrimidinyl>-2(S)-(O-benzoylmethyl)tetrahydrofuran

Chemical Property of 4(S)-<4-amino-2-oxo-1(2H)-pyrimidinyl>-2(S)-(O-benzoylmethyl)tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4(S)-<4-amino-2-oxo-1(2H)-pyrimidinyl>-2(S)-(O-benzoylmethyl)tetrahydrofuran

There total 11 articles about 4(S)-<4-amino-2-oxo-1(2H)-pyrimidinyl>-2(S)-(O-benzoylmethyl)tetrahydrofuran 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: 66.0%

2(S)-(O-benzoylmethyl)-4(S)-<4-(1,2,4-triazolyl)-2-oxo-1(2H)-pyrimidinyl>tetrahydrofuran (143191-80-4) → 4(S)-<4-amino-2-oxo-1(2H)-pyrimidinyl>-2(S)-(O-benzoylmethyl)tetrahydrofuran (151223-92-6)

Guidance literature:

With ammonium hydroxide; In 1,4-dioxane; for 14h; Ambient temperature;

DOI:10.1016/S0040-4020(01)85259-5

Reference yield:

1,2,4-Triazole (288-88-0) + triazolo nucleoside + 4(S)-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>tetrahydro-2(S)-furanmethanol benzoate (143191-79-1) + 4-chlorophenylphosphorodichloridate (772-79-2) → 4(S)-<4-amino-2-oxo-1(2H)-pyrimidinyl>-2(S)-(O-benzoylmethyl)tetrahydrofuran (151223-92-6)

Guidance literature:

In 1,4-dioxane; pyridine; methanol; ammonium hydroxide; dichloromethane;

Reference yield:

[(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate (4105-29-7) → 4(S)-<4-amino-2-oxo-1(2H)-pyrimidinyl>-2(S)-(O-benzoylmethyl)tetrahydrofuran (151223-92-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / hydrogen chloride / methanol / 12 h / Ambient temperature

2: 1.) chlorotrimethylsilane; 2.) triethylsilane, TMS-triflate / 1.) 1,1,1,3,3,3-hexamethyldisilazane, reflux, 17 h; 2.) CH₃CN, r.t., 17 h

3: 89 percent / pyridine / 31 h / 5 °C

4: 43 percent / potassium carbonate, 18-crown-6 / dimethylformamide / 11 h / 75 °C

5: 46 percent / 4-chlorophenylphosphorodichloridate / pyridine / 26 h / Ambient temperature

6: 66 percent / NH₄OH / dioxane / 14 h / Ambient temperature

With hydrogenchloride; triethylsilane; ammonium hydroxide; chloro-trimethyl-silane; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; 4-chlorophenylphosphorodichloridate; In 1,4-dioxane; pyridine; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)85259-5

upstream raw materials:

2(S)-(O-benzoylmethyl)-4(S)-<4-(1,2,4-triazolyl)-2-oxo-1(2H)-pyrimidinyl>tetrahydrofuran

[(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate

benzoyl chloride

1,2-O-isopropylidene-α-D-xylose