(4S,5R)-4-cyclohexylmethyl-5-<(1'S)-1'-hydroxy-3-methylbutyl>oxazolidin-2-one

Base Information

• Chemical Name: (4S,5R)-4-cyclohexylmethyl-5-<(1'S)-1'-hydroxy-3-methylbutyl>oxazolidin-2-one
• CAS No.: 117161-13-4
• Molecular Formula: C₁₅H₂₇NO₃
• Molecular Weight: 269.384
• Mol file: 117161-13-4.mol

Synonyms:(4S,5R)-4-cyclohexylmethyl-5-<(1'S)-1'-hydroxy-3-methylbutyl>oxazolidin-2-one

Chemical Property of (4S,5R)-4-cyclohexylmethyl-5-<(1'S)-1'-hydroxy-3-methylbutyl>oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-4-cyclohexylmethyl-5-<(1'S)-1'-hydroxy-3-methylbutyl>oxazolidin-2-one

There total 15 articles about (4S,5R)-4-cyclohexylmethyl-5-<(1'S)-1'-hydroxy-3-methylbutyl>oxazolidin-2-one 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: 83.0%

(2S,3R,4S)-2-[(tert-butyloxycarbonyl)amino]-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (104882-10-2) → (4S,5R)-4-cyclohexylmethyl-5-<(1'S)-1'-hydroxy-3-methylbutyl>oxazolidin-2-one (117161-13-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 3h;

DOI:10.1021/jm00120a005

Reference yield: 51.0%

(4S,5R)-3-Benzyl-4-cyclohexylmethyl-5-<(S)-(1-hydroxy-3-methyl)butyl>oxazolidin-2-one (131451-97-3) → (4S,5R)-4-cyclohexylmethyl-5-<(1'S)-1'-hydroxy-3-methylbutyl>oxazolidin-2-one (117161-13-4)

Guidance literature:

With ammonia; sodium; at -78 ℃; for 2h;

DOI:10.1246/cl.1990.1709

Reference yield:

(4R,5R)-4-<(S)-(1-(N-Benzyl-N-methoxycarbonyl)amino-2-cyclohexyl)ethyl>-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane (139056-96-5,139164-19-5) → (4S,5R)-4-cyclohexylmethyl-5-<(1'S)-1'-hydroxy-3-methylbutyl>oxazolidin-2-one (117161-13-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 80percent AcOH / 5 h / 80 °C

2: KOH / methanol / 3.5 h / Ambient temperature

3: 96 percent / pyridine / 3 h / 0 °C

4: 98 percent / H₂ / 20percent Pd(OH)2/C / methanol / 48 h / 760 Torr / Ambient temperature

5: 94 percent / NaOMe / tetrahydrofuran / 0.5 h / 0 °C

6: 1) CuI / 1) Et₂O, 10 min, 0 deg C, 2) Et₂O, 0 deg C, 1.5 h

7: 51 percent / Na, liq. NH₃ / diethyl ether / 2 h / -78 °C

With pyridine; potassium hydroxide; copper(l) iodide; ammonia; hydrogen; sodium methylate; sodium; acetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1248/cpb.39.2550

upstream raw materials:

(2S,3R,4S)-2-[(tert-butyloxycarbonyl)amino]-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

(4S,5R)-3-Benzyl-4-cyclohexylmethyl-5-<(S)-(1-hydroxy-3-methyl)butyl>oxazolidin-2-one

2-Cyclohexyl-1-((2R,3R)-3-isobutyl-oxiranyl)-ethanone

2(S)-t-Butyloxycarbonylamino-1-cyclohexyl-6-methylhept-3-ene

Downstream raw materials:

(S)-2-amino-1-cyclohexyl-(R)-3,(S)-4-dihydroxy-6-methylheptane hydrochloride

(2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

(2S,3R,4S)-2-[(tert-butyloxycarbonyl)amino]-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

(S)-2-Cyclohexyl-1-((4R,5S)-5-isobutyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethylamine