methyl (3S,4S)-4-tert-butoxycarbonylamino-5-cyclohexylmethyl-3-hydroxypentanoate

Base Information

Chemical Name:methyl (3S,4S)-4-tert-butoxycarbonylamino-5-cyclohexylmethyl-3-hydroxypentanoate
CAS No.:101669-82-3
Molecular Formula:C₁₇H₃₁NO₅
Molecular Weight:329.437
Hs Code.:

Synonyms:methyl (3S,4S)-4-tert-butoxycarbonylamino-5-cyclohexylmethyl-3-hydroxypentanoate

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Chemical Property of methyl (3S,4S)-4-tert-butoxycarbonylamino-5-cyclohexylmethyl-3-hydroxypentanoate

Chemical Property:

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Technology Process of methyl (3S,4S)-4-tert-butoxycarbonylamino-5-cyclohexylmethyl-3-hydroxypentanoate

There total 15 articles about methyl (3S,4S)-4-tert-butoxycarbonylamino-5-cyclohexylmethyl-3-hydroxypentanoate 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%

: 101669-80-1
methyl (3S,4S)-N-tert-butoxycarbonyl-4-amino-3-hydroxy-5-phenylpentanoate

: 101669-82-3
methyl (3S,4S)-4-tert-butoxycarbonylamino-5-cyclohexylmethyl-3-hydroxypentanoate

Guidance literature:: With hydrogen; Rh/Al₂O₃; In methanol;

Reference yield:

: 178421-69-7
(2S,3S)-3-azido-4-cyclohexyl-1,2-butanediol

: 101669-82-3
methyl (3S,4S)-4-tert-butoxycarbonylamino-5-cyclohexylmethyl-3-hydroxypentanoate

Guidance literature:: Multi-step reaction with 10 steps

1: 97 percent / H₂ / 10percentPd/C / ethyl acetate / 18 h / Ambient temperature

2: 76 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

3: 97 percent / triethylamine, 4-dimethylaminopyridne / CH₂Cl₂ / -15 - 20 °C

4: 1.) tetrabutylammonium fluoride, 2.) sodium methoxide / 1.) THF, RT, 30 min, 2.) THF, RT, 2 h

5: 80 percent / NEt₃ / tetrahydrofuran / 22 h / Ambient temperature

6: 81 percent / p-toluenesulphonic acid / benzene / 0.5 h / Heating

7: 77 percent / DIBAL-H / benzene; diethyl ether / 0.25 h / -40 °C

8: 5 percent aq. NaH₂PO₄, 1 M aq. KMNO₄ / 2-methyl-propan-2-ol / Ambient temperature

9: diethyl ether / Ambient temperature

10: 85 percent aq. acetic acid / 0.67 h / 70 °C

With 1H-imidazole; dmap; potassium permanganate; sodium dihydrogenphosphate; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; 10% palladium on active carbon; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1016/0040-4020(96)00328-6

Reference yield:

: (2R,3R)-3-cyclohexyl-2,3-epoxy-1-butanol

: 101669-82-3
methyl (3S,4S)-4-tert-butoxycarbonylamino-5-cyclohexylmethyl-3-hydroxypentanoate

Guidance literature:: Multi-step reaction with 11 steps

1: 99 percent / titanium diazidodiisopropoxide / benzene / 20 - 75 °C

2: 97 percent / H₂ / 10percentPd/C / ethyl acetate / 18 h / Ambient temperature

3: 76 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

4: 97 percent / triethylamine, 4-dimethylaminopyridne / CH₂Cl₂ / -15 - 20 °C

5: 1.) tetrabutylammonium fluoride, 2.) sodium methoxide / 1.) THF, RT, 30 min, 2.) THF, RT, 2 h

6: 80 percent / NEt₃ / tetrahydrofuran / 22 h / Ambient temperature

7: 81 percent / p-toluenesulphonic acid / benzene / 0.5 h / Heating

8: 77 percent / DIBAL-H / benzene; diethyl ether / 0.25 h / -40 °C

9: 5 percent aq. NaH₂PO₄, 1 M aq. KMNO₄ / 2-methyl-propan-2-ol / Ambient temperature

10: diethyl ether / Ambient temperature

11: 85 percent aq. acetic acid / 0.67 h / 70 °C

With 1H-imidazole; dmap; potassium permanganate; sodium dihydrogenphosphate; diisopropoxytitanium diazide; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; 10% palladium on active carbon; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1016/0040-4020(96)00328-6