(3S,4R)-4-[(tert-butyloxycarbonyl)amino]-5-cyclohexyl-3-hydroxypentanoic acid ethyl ester

Base Information

• Chemical Name: (3S,4R)-4-[(tert-butyloxycarbonyl)amino]-5-cyclohexyl-3-hydroxypentanoic acid ethyl ester
• CAS No.: 607685-52-9
• Molecular Formula: C₁₈H₃₃NO₅
• Molecular Weight: 343.464
• Mol file: 607685-52-9.mol

Synonyms:(3S,4R)-4-[(tert-butyloxycarbonyl)amino]-5-cyclohexyl-3-hydroxypentanoic acid ethyl ester

Chemical Property of (3S,4R)-4-[(tert-butyloxycarbonyl)amino]-5-cyclohexyl-3-hydroxypentanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-4-[(tert-butyloxycarbonyl)amino]-5-cyclohexyl-3-hydroxypentanoic acid ethyl ester

There total 10 articles about (3S,4R)-4-[(tert-butyloxycarbonyl)amino]-5-cyclohexyl-3-hydroxypentanoic 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: 95.0%

ethanol (64-17-5) + (4S,5R)-1-(tert-butyloxycarbonyl)-4-hydroxy-5-cyclohexylmethyl-2-pyrrolidinone (607685-51-8) → (3S,4R)-4-[(tert-butyloxycarbonyl)amino]-5-cyclohexyl-3-hydroxypentanoic acid ethyl ester (607685-52-9)

Guidance literature:

With potassium cyanide; In tetrahydrofuran; at 20 ℃; for 36h;

DOI:10.1016/S0957-4166(03)00442-7

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → (3S,4R)-4-[(tert-butyloxycarbonyl)amino]-5-cyclohexyl-3-hydroxypentanoic acid ethyl ester (607685-52-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / H₂, acetic acid / PtO₂ / H₂O / 18 h / 50 °C / 2327.2 Torr

2: 100 percent / 0.5 N aq. NaOH / dioxane / 1.) from 0deg C to RT, 3 h, 2.) RT, 17 h

3: 1.) N,N'-carbonyldiimidazole / 1.) THF, RT, 20 h, 2.) RT, 3.5 h

4: sodium cyanoborohydride, acetic acid / tetrahydrofuran / 16 h / Ambient temperature

With sodium hydroxide; hydrogen; sodium cyanoborohydride; acetic acid; 1,1'-carbonyldiimidazole; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/jo00239a036

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (3S,4R)-4-[(tert-butyloxycarbonyl)amino]-5-cyclohexyl-3-hydroxypentanoic acid ethyl ester (607685-52-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / DMAP; Et₃N / tetrahydrofuran / 14 h / 20 °C

2: 91 percent / formic acid / Pd/C / methanol / 2 h / 20 °C

3: 95 percent / KCN / tetrahydrofuran / 36 h / 20 °C

With dmap; potassium cyanide; formic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1016/S0957-4166(03)00442-7

upstream raw materials:

3-oxo-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester

ethanol

(4S,5R)-1-(tert-butyloxycarbonyl)-4-hydroxy-5-cyclohexylmethyl-2-pyrrolidinone

di-tert-butyl dicarbonate