(2S,3S,4R)-5-cyclohexyl-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methylpentanoic acid

Base Information

Chemical Name:(2S,3S,4R)-5-cyclohexyl-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methylpentanoic acid
CAS No.:1315271-30-7
Molecular Formula:C₂₇H₃₃NO₅
Molecular Weight:451.563
Hs Code.:

Synonyms:(2S,3S,4R)-5-cyclohexyl-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methylpentanoic acid

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Chemical Property of (2S,3S,4R)-5-cyclohexyl-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methylpentanoic acid

Chemical Property:

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Technology Process of (2S,3S,4R)-5-cyclohexyl-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methylpentanoic acid

There total 6 articles about (2S,3S,4R)-5-cyclohexyl-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methylpentanoic 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:

: C₁₂H₂₃NO₃

: 82911-69-1
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

: 1315271-30-7
(2S,3S,4R)-5-cyclohexyl-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methylpentanoic acid

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;
DOI:10.1016/j.bmc.2011.04.047

Reference yield:

: 127095-92-5
N-tert-butoxycarbonyl-D-cyclohexylalanine

: 1315271-30-7
(2S,3S,4R)-5-cyclohexyl-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methylpentanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: triethylamine / dichloromethane / Inert atmosphere

1.2: Inert atmosphere

1.3: Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere

3.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 - 0 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

3.3: 4 h / 0 °C

4.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 4 h / 0 °C

5.1: dimethylsulfide; trifluoroacetic acid / 0.5 h / 20 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

With lithium aluminium tetrahydride; dimethylsulfide; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.bmc.2011.04.047

Reference yield:

: 1315271-16-9
(2R,3S,4S,4'S)-[2-cyclohexyl-3-hydroxy-5-(4'-isopropyl-2'-oxo-oxazolidin-3'-yl)-4-methyl-5-oxo-2-pentyl]carbamic acid tert-butyl ester

: 1315271-30-7
(2S,3S,4R)-5-cyclohexyl-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methylpentanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 4 h / 0 °C

2: dimethylsulfide; trifluoroacetic acid / 0.5 h / 20 °C / Inert atmosphere

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

With dimethylsulfide; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.bmc.2011.04.047