(S)-2-{4-[3-(2-Amino-4-hydroxy-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-propyl]-benzoylamino}-pentanedioic acid diethyl ester

Base Information

• Chemical Name: (S)-2-{4-[3-(2-Amino-4-hydroxy-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-propyl]-benzoylamino}-pentanedioic acid diethyl ester
• CAS No.: 1053704-34-9
• Molecular Formula: C₂₆H₃₄N₄O₆
• Molecular Weight: 498.579
• Mol file: 1053704-34-9.mol

Synonyms:(S)-2-{4-[3-(2-Amino-4-hydroxy-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-propyl]-benzoylamino}-pentanedioic acid diethyl ester

Chemical Property of (S)-2-{4-[3-(2-Amino-4-hydroxy-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-propyl]-benzoylamino}-pentanedioic acid diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{4-[3-(2-Amino-4-hydroxy-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-propyl]-benzoylamino}-pentanedioic acid diethyl ester

There total 9 articles about (S)-2-{4-[3-(2-Amino-4-hydroxy-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-propyl]-benzoylamino}-pentanedioic acid diethyl 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:

4-(tert-butoxycarbonyl)benzaldehyde (65874-27-3) → (S)-2-{4-[3-(2-Amino-4-hydroxy-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-propyl]-benzoylamino}-pentanedioic acid diethyl ester (1053704-34-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h

2: H₂ / 10percent Pd/C

3: 1N aq. NaOH / ethanol / 3 h / Ambient temperature

4: 97 percent / NaBH₄, BF₃*Et₂O / tetrahydrofuran / Ambient temperature

5: 45 g / triethylamine / CH₂Cl₂ / 1 h

6: 95 percent / NaI / acetone / 12 h / Heating

7: 56 percent / tributyltin hydride, AIBN / benzene / Heating

8: 21.4 percent / potassium tert-butoxide / 2-methyl-propan-2-ol / 5 h / Heating

9: 1N HCl / acetic acid / Ambient temperature

10: DPPA, Et₃N / dimethylformamide / 1.) ice-bath cooling, 30 min, 2.) RT

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; diphenyl-phosphinic acid; potassium tert-butylate; hydrogen; tri-n-butyl-tin hydride; sodium hydride; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/jm00037a012

Reference yield:

ethyl 3-<4-(tert-butoxycarbonyl)phenyl>acrylate (149325-50-8) → (S)-2-{4-[3-(2-Amino-4-hydroxy-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-propyl]-benzoylamino}-pentanedioic acid diethyl ester (1053704-34-9)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂ / 10percent Pd/C

2: 1N aq. NaOH / ethanol / 3 h / Ambient temperature

3: 97 percent / NaBH₄, BF₃*Et₂O / tetrahydrofuran / Ambient temperature

4: 45 g / triethylamine / CH₂Cl₂ / 1 h

5: 95 percent / NaI / acetone / 12 h / Heating

6: 56 percent / tributyltin hydride, AIBN / benzene / Heating

7: 21.4 percent / potassium tert-butoxide / 2-methyl-propan-2-ol / 5 h / Heating

8: 1N HCl / acetic acid / Ambient temperature

9: DPPA, Et₃N / dimethylformamide / 1.) ice-bath cooling, 30 min, 2.) RT

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; diphenyl-phosphinic acid; potassium tert-butylate; hydrogen; tri-n-butyl-tin hydride; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/jm00037a012

Reference yield:

tert-Butyl 4-(3-hydroxy-1-propyl)benzoate (126931-32-6) → (S)-2-{4-[3-(2-Amino-4-hydroxy-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-propyl]-benzoylamino}-pentanedioic acid diethyl ester (1053704-34-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 45 g / triethylamine / CH₂Cl₂ / 1 h

2: 95 percent / NaI / acetone / 12 h / Heating

3: 56 percent / tributyltin hydride, AIBN / benzene / Heating

4: 21.4 percent / potassium tert-butoxide / 2-methyl-propan-2-ol / 5 h / Heating

5: 1N HCl / acetic acid / Ambient temperature

6: DPPA, Et₃N / dimethylformamide / 1.) ice-bath cooling, 30 min, 2.) RT

With hydrogenchloride; 2,2'-azobis(isobutyronitrile); diphenyl-phosphinic acid; potassium tert-butylate; tri-n-butyl-tin hydride; triethylamine; sodium iodide; In dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/jm00037a012

upstream raw materials:

4-(tert-butoxycarbonyl)benzaldehyde

tert-Butyl 4-(3-hydroxy-1-propyl)benzoate

tert-butyl 4-(3-iodopropyl)benzoate

3-<4-(tert-butoxycarbonyl)phenyl>propionic acid