(3R,4S)-4-tert-Butoxycarbonylamino-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid

Base Information

Chemical Name:(3R,4S)-4-tert-Butoxycarbonylamino-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid
CAS No.:118233-28-6
Molecular Formula:C₁₆H₂₇F₂NO₅
Molecular Weight:351.391
Hs Code.:

Synonyms:(3R,4S)-4-tert-Butoxycarbonylamino-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid

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Chemical Property of (3R,4S)-4-tert-Butoxycarbonylamino-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid

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Technology Process of (3R,4S)-4-tert-Butoxycarbonylamino-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid

There total 3 articles about (3R,4S)-4-tert-Butoxycarbonylamino-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid 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: 79.0%

: 103322-58-3
ethyl 4(S)-<(tert-butyloxycarbonyl)amino>-5-(cyclohexylmethyl)-2,2-difluoro-3(R)-hydroxypentanoate

: 118233-28-6
(3R,4S)-4-tert-Butoxycarbonylamino-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; for 4h;
DOI:10.1021/jm00079a001

Reference yield:

: 37736-82-6
(S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid

: 118233-28-6
(3R,4S)-4-tert-Butoxycarbonylamino-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1: HATU; Et₃N / CH₂Cl₂ / 3 h / 20 °C

2: LiAlH₄ / diethyl ether / 0.33 h

3: 64 percent / Zn / tetrahydrofuran / 0.5 h / Heating

4: LiOH / acetonitrile / 2 h

With lithium hydroxide; lithium aluminium tetrahydride; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; 1: Condensation / 2: Reduction / 3: Reformatsky reaction / 4: Hydrolysis;
DOI:10.1021/jm000100f

Reference yield:

: 115766-13-7
(S)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-N-methoxy-N-methylcyclohexanepropanamide

: 118233-28-6
(3R,4S)-4-tert-Butoxycarbonylamino-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: LiAlH₄ / diethyl ether / 0.33 h

2: 64 percent / Zn / tetrahydrofuran / 0.5 h / Heating

3: LiOH / acetonitrile / 2 h

With lithium hydroxide; lithium aluminium tetrahydride; zinc; In tetrahydrofuran; diethyl ether; acetonitrile; 1: Reduction / 2: Reformatsky reaction / 3: Hydrolysis;
DOI:10.1021/jm000100f