((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-carbamic acid ethyl ester

Base Information

• Chemical Name: ((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-carbamic acid ethyl ester
• CAS No.: 156540-64-6
• Molecular Formula: C₁₇H₃₃NO₄
• Molecular Weight: 315.453
• Mol file: 156540-64-6.mol

Synonyms:((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-carbamic acid ethyl ester

Chemical Property of ((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-carbamic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-carbamic acid ethyl ester

There total 12 articles about ((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-carbamic acid ethyl 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:

((1S,2R)-1-Cyclohexylmethyl-2-hydroxy-5-methyl-3-oxo-hexyl)-carbamic acid ethyl ester (167823-30-5) → ((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-carbamic acid ethyl ester (156540-64-6)

Guidance literature:

With sodium tris(acetoxy)borohydride; In n-heptane; acetonitrile; at 20 - 24 ℃; for 4h;

DOI:10.1021/jo960694n

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → ((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-carbamic acid ethyl ester (156540-64-6)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂ / Rh-Pd-C / propan-2-ol / 50 °C / 2585.7 Torr

2: 1) N-methylpiperidine, ethyl chloroformate, 2) N-methylpiperidine / 1) CH₂Cl₂, -40 deg C, 2 h, 2) CH₂Cl₂, -30 deg C -> 20 deg C; 20 deg C, 8 h

3: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 1.5 h / -15 °C

4: acetone cyanohydrin, tetrabutylammonium iodide / H₂O; heptane / 25 °C

5: 132.8 g / HCl / H₂O / 3 h / 80 °C

6: NaOH / H₂O / 2.5 h / 5 °C

7: LiBr / toluene; tetrahydrofuran; pentane / 2 h / 5 - 10 °C

8: 7.1 kg / NaB(O₂CCH₃)3H / heptane; acetonitrile / 4 h / 20 - 24 °C

With N-methylcyclohexylamine; hydrogenchloride; sodium hydroxide; hydrogen; chloroformic acid ethyl ester; tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; 2-hydroxy-2-methylpropanenitrile; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium bromide; Rh-Pd on carbon; In tetrahydrofuran; n-heptane; water; isopropyl alcohol; toluene; acetonitrile; pentane;

DOI:10.1021/jo960694n

Reference yield:

(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal (98105-42-1) → ((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-carbamic acid ethyl ester (156540-64-6)

Guidance literature:

Multi-step reaction with 5 steps

1: acetone cyanohydrin, tetrabutylammonium iodide / H₂O; heptane / 25 °C

2: 132.8 g / HCl / H₂O / 3 h / 80 °C

3: NaOH / H₂O / 2.5 h / 5 °C

4: LiBr / toluene; tetrahydrofuran; pentane / 2 h / 5 - 10 °C

5: 7.1 kg / NaB(O₂CCH₃)3H / heptane; acetonitrile / 4 h / 20 - 24 °C

With hydrogenchloride; sodium hydroxide; tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; 2-hydroxy-2-methylpropanenitrile; lithium bromide; In tetrahydrofuran; n-heptane; water; toluene; acetonitrile; pentane;

DOI:10.1021/jo960694n

upstream raw materials:

((Z)-(S)-1-Cyclohexylmethyl-5-methyl-hex-2-enyl)-carbamic acid ethyl ester

((1S,2R)-1-Cyclohexylmethyl-2-hydroxy-5-methyl-3-oxo-hexyl)-carbamic acid ethyl ester

N-tert-butoxycarbonyl-L-phenylalanine

(S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid

Downstream raw materials:

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