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

Base Information

Chemical Name:(R)-2-Benzyloxycarbonylamino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester
CAS No.:288404-39-7
Molecular Formula:C₁₉H₂₇NO₄
Molecular Weight:333.428
Hs Code.:

Synonyms:(R)-2-Benzyloxycarbonylamino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester

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Chemical Property of (R)-2-Benzyloxycarbonylamino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester

Chemical Property:

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Technology Process of (R)-2-Benzyloxycarbonylamino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester

There total 1 articles about (R)-2-Benzyloxycarbonylamino-2-isopropyl-5-methyl-hex-4-enoic acid methyl 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: 93.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 145452-08-0
(R)-2-Amino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester

: 288404-39-7
(R)-2-Benzyloxycarbonylamino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1021/ol0059293

Reference yield: 95.0%

: 288404-39-7
(R)-2-Benzyloxycarbonylamino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester

: 288404-41-1
(R)-2-Benzyloxycarbonylamino-3-methyl-2-(2-oxo-ethyl)-butyric acid methyl ester

Guidance literature:: With ozone; triphenylphosphine; at -78 ℃;
DOI:10.1021/ol0059293

Reference yield:

: 288404-39-7
(R)-2-Benzyloxycarbonylamino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester

: 159216-07-6
CHCH₂CCOCH₂C₆H₅NCO₂C₄H₉NCC₃H₇COCCHNHCC₄H₉CH₂COHCONCC₄H₉COCH₂CNCCH₂C₆H₅COCH₃CH₂CHC₃H₅

Guidance literature:: Multi-step reaction with 14 steps

1: 95 percent / O₃; PPh₃ / -78 °C

2: 78 percent / NaBH₃CN; aq. HCl / methanol / 3 h / 20 °C

3: 83 percent / H₂ / Pd(C) / ethanol / 1 h

4: toluene

5: 77 percent / KHMDS; 18-crown-6 / tetrahydrofuran / 3 h / 20 °C

6: 85 percent / (COCl)2; DMSO; DBU / CH₂Cl₂ / 0.33 h / 20 °C

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

8: 77 percent / KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 4 h / 20 °C

9: 80 percent / (COCl)2; DMSO; DBU / CH₂Cl₂ / 0.33 h / 20 °C

10: (MeO)3CH / tetrahydrofuran

11: KHMDS; 18-crown-6

12: 65 percent / (COCl)2; DMSO; DBU / CH₂Cl₂ / 0.33 h / 20 °C

13: (MeO)3CH / tetrahydrofuran

14: 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; triphenylphosphine; trimethyl orthoformate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; 1: Oxidation / 2: Reduction / 3: Hydrogenation / 4: Condensation / 5: Ring cleavage / 6: Swern oxidation / 7: Condensation / 8: Cyclization / 9: Swern oxidation / 10: Condensation / 11: Cyclization / 12: Swern oxidation / 13: Condensation / 14: Cyclization;
DOI:10.1021/ol0059293