CHCH₂CCOCH₂C₆H₅NCO₂C₄H₉NCC₃H₇COCCHNHCC₄H₉CH₂COHCONCC₄H₉COCH₂CNCCH₂C₆H₅COCH₃CH₂CHC₃H₅

Base Information

• Chemical Name: CHCH₂CCOCH₂C₆H₅NCO₂C₄H₉NCC₃H₇COCCHNHCC₄H₉CH₂COHCONCC₄H₉COCH₂CNCCH₂C₆H₅COCH₃CH₂CHC₃H₅
• CAS No.: 159216-07-6
• Molecular Formula: C₅₄H₆₉N₅O₈
• Molecular Weight: 916.171

Synonyms:CHCH₂CCOCH₂C₆H₅NCO₂C₄H₉NCC₃H₇COCCHNHCC₄H₉CH₂COHCONCC₄H₉COCH₂CNCCH₂C₆H₅COCH₃CH₂CHC₃H₅

Chemical Property of CHCH₂CCOCH₂C₆H₅NCO₂C₄H₉NCC₃H₇COCCHNHCC₄H₉CH₂COHCONCC₄H₉COCH₂CNCCH₂C₆H₅COCH₃CH₂CHC₃H₅

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Technology Process of CHCH₂CCOCH₂C₆H₅NCO₂C₄H₉NCC₃H₇COCCHNHCC₄H₉CH₂COHCONCC₄H₉COCH₂CNCCH₂C₆H₅COCH₃CH₂CHC₃H₅

There total 52 articles about CHCH₂CCOCH₂C₆H₅NCO₂C₄H₉NCC₃H₇COCCHNHCC₄H₉CH₂COHCONCC₄H₉COCH₂CNCCH₂C₆H₅COCH₃CH₂CHC₃H₅ 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: 64.0%

CHCH2CCO2CH3CH2C6H5NCO2C4H9NCC3H7COCCHNHCC4H9CH2COHCONCC4H9COCH2CNCCH2C6H5COCH3CH2CHC3H6 → CHCH2CCOCH2C6H5NCO2C4H9NCC3H7COCCHNHCC4H9CH2COHCONCC4H9COCH2CNCCH2C6H5COCH3CH2CHC3H5 (159216-07-6)

Guidance literature:

With potassium hexamethylsilazane;

DOI:10.1021/ol0059293

Reference yield:

(S)-2-Amino-2-isobutyl-5-methyl-hex-4-enoic acid methyl ester (145452-11-5) → CHCH2CCOCH2C6H5NCO2C4H9NCC3H7COCCHNHCC4H9CH2COHCONCC4H9COCH2CNCCH2C6H5COCH3CH2CHC3H5 (159216-07-6)

Guidance literature:

Multi-step reaction with 12 steps

1: i-Pr₂NEt / tetrahydrofuran / 4 h / 20 °C

2: O₃; Ph₃P / CH₂Cl₂ / -78 °C

3: 80 percent / NaBH₃CN; aq. HCl / methanol / 3 h / 20 °C

4: 84 percent / H₂ / Pd(C) / ethanol / 1 h

5: (MeO)3CH / tetrahydrofuran / 14 h / 20 °C

6: 77 percent / KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 4 h / 20 °C

7: 80 percent / (COCl)2; DMSO; DBU / CH₂Cl₂ / 0.33 h / 20 °C

8: (MeO)3CH / tetrahydrofuran

9: KHMDS; 18-crown-6

10: 65 percent / (COCl)2; DMSO; DBU / CH₂Cl₂ / 0.33 h / 20 °C

11: (MeO)3CH / tetrahydrofuran

12: 64 percent / KHMDS

With hydrogenchloride; oxalyl dichloride; 18-crown-6 ether; hydrogen; potassium hexamethylsilazane; sodium cyanoborohydride; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trimethyl orthoformate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; 1: benzyloxycarbonylation / 2: Oxidation / 3: Reduction / 4: Hydrogenation / 5: Condensation / 6: Cyclization / 7: Swern oxidation / 8: Condensation / 9: Cyclization / 10: Swern oxidation / 11: Condensation / 12: Cyclization;

DOI:10.1021/ol0059293

Reference yield:

(R)-2-Amino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester (145452-08-0) → CHCH2CCOCH2C6H5NCO2C4H9NCC3H7COCCHNHCC4H9CH2COHCONCC4H9COCH2CNCCH2C6H5COCH3CH2CHC3H5 (159216-07-6)

Guidance literature:

Multi-step reaction with 15 steps

1: 93 percent / i-Pr₂NEt / tetrahydrofuran / 4 h / 20 °C

2: 95 percent / O₃; PPh₃ / -78 °C

3: 78 percent / NaBH₃CN; aq. HCl / methanol / 3 h / 20 °C

4: 83 percent / H₂ / Pd(C) / ethanol / 1 h

5: toluene

6: 77 percent / KHMDS; 18-crown-6 / tetrahydrofuran / 3 h / 20 °C

7: 85 percent / (COCl)2; DMSO; DBU / CH₂Cl₂ / 0.33 h / 20 °C

8: (MeO)3CH / tetrahydrofuran / 14 h / 20 °C

9: 77 percent / KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 4 h / 20 °C

10: 80 percent / (COCl)2; DMSO; DBU / CH₂Cl₂ / 0.33 h / 20 °C

11: (MeO)3CH / tetrahydrofuran

12: KHMDS; 18-crown-6

13: 65 percent / (COCl)2; DMSO; DBU / CH₂Cl₂ / 0.33 h / 20 °C

14: (MeO)3CH / tetrahydrofuran

15: 64 percent / KHMDS

With hydrogenchloride; oxalyl dichloride; 18-crown-6 ether; hydrogen; potassium hexamethylsilazane; sodium cyanoborohydride; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trimethyl orthoformate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; 1: benzyloxycarbonylation / 2: Oxidation / 3: Reduction / 4: Hydrogenation / 5: Condensation / 6: Ring cleavage / 7: Swern oxidation / 8: Condensation / 9: Cyclization / 10: Swern oxidation / 11: Condensation / 12: Cyclization / 13: Swern oxidation / 14: Condensation / 15: Cyclization;

DOI:10.1021/ol0059293

upstream raw materials:

(S)-2-tert-Butoxycarbonylamino-2-[(R)-5-isopropyl-4-oxo-5-(2-oxo-ethyl)-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester

(S)-2-tert-Butoxycarbonylamino-2-[(2S,5'S)-5'-isobutyl-2-isopropyl-3,4'-dioxo-5'-(2-oxo-ethyl)-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-4-yl]-3-phenyl-propionic acid methyl ester

(R)-2-Amino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester

(S)-2-Amino-2-isobutyl-5-methyl-hex-4-enoic acid methyl ester

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