(2R,3R,4R,5S)-5-Amino-6-cyclohexyl-3,4-dihydroxy-2-isobutyl-hexanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide

Base Information

• Chemical Name: (2R,3R,4R,5S)-5-Amino-6-cyclohexyl-3,4-dihydroxy-2-isobutyl-hexanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide
• CAS No.: 146363-05-5
• Molecular Formula: C₂₈H₄₈N₄O₄
• Molecular Weight: 504.714
• Mol file: 146363-05-5.mol

Synonyms:

Chemical Property of (2R,3R,4R,5S)-5-Amino-6-cyclohexyl-3,4-dihydroxy-2-isobutyl-hexanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S)-5-Amino-6-cyclohexyl-3,4-dihydroxy-2-isobutyl-hexanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide

There total 6 articles about (2R,3R,4R,5S)-5-Amino-6-cyclohexyl-3,4-dihydroxy-2-isobutyl-hexanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide 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:

{(S)-2-Cyclohexyl-1-[(4R,5R)-2,2-dimethyl-5-((R)-3-methyl-1-{(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butylcarbamoyl}-butyl)-[1,3]dioxolan-4-yl]-ethyl}-carbamic acid tert-butyl ester → (2R,3R,4R,5S)-5-Amino-6-cyclohexyl-3,4-dihydroxy-2-isobutyl-hexanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide (146363-05-5)

Guidance literature:

With ethandithiol; acetyl chloride; In methanol; for 5h;

DOI:10.1021/jm00112a005

Reference yield:

tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (117997-58-7) → (2R,3R,4R,5S)-5-Amino-6-cyclohexyl-3,4-dihydroxy-2-isobutyl-hexanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide (146363-05-5)

Guidance literature:

Multi-step reaction with 5 steps

2: 65 percent / aq. hydrogen peroxide, aq. lithium hydroxide / methanol / 4 h / Ambient temperature

3: 1.) camphorsulfonic acid, 2.) acetone / 1.) CH₂Cl₂, RT, 45 min, 2.) CH₂Cl₂, RT, 14 h

4: diisopropylethylamine, diethylphosphoryl cyanide / CH₂Cl₂ / 14 h / Ambient temperature

5: acetyl chloride, ethanedithiol / methanol / 5 h

With ethandithiol; lithium hydroxide; diethylphosphoryl cyanide; camphor-10-sulfonic acid; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; acetyl chloride; acetone; In methanol; dichloromethane;

DOI:10.1021/jm00112a005

Reference yield:

(4R,5S)-4-methyl-3-(4-methylpentanoyl)-5-phenyl-oxazolidin-2-one (134458-52-9) → (2R,3R,4R,5S)-5-Amino-6-cyclohexyl-3,4-dihydroxy-2-isobutyl-hexanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide (146363-05-5)

Guidance literature:

Multi-step reaction with 5 steps

2: 65 percent / aq. hydrogen peroxide, aq. lithium hydroxide / methanol / 4 h / Ambient temperature

3: 1.) camphorsulfonic acid, 2.) acetone / 1.) CH₂Cl₂, RT, 45 min, 2.) CH₂Cl₂, RT, 14 h

4: diisopropylethylamine, diethylphosphoryl cyanide / CH₂Cl₂ / 14 h / Ambient temperature

5: acetyl chloride, ethanedithiol / methanol / 5 h

With ethandithiol; lithium hydroxide; diethylphosphoryl cyanide; camphor-10-sulfonic acid; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; acetyl chloride; acetone; In methanol; dichloromethane;

DOI:10.1021/jm00112a005

upstream raw materials:

tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate

(4R,5S)-4-methyl-3-(4-methylpentanoyl)-5-phenyl-oxazolidin-2-one

3(R)-<3-(tert-butyloxycarbonyl)-4(S)-(cyclohexylmethyl)-2,2-dimethyl-5(R)-oxazolidinyl>-3-hydroxy-2(R)-isobutylpropanoic acid

3-<3(R)-<3-(tert-butyloxycarbonyl)-4(S)-(cyclohexylmethyl)-2,2-dimethyl-5(R)-oxazolidinyl>-3-hydroxy-2(R)-isobutyl-1-oxopropyl>-4(R)-methyl-5(S)-phenyl-2-oxazolidinone

Downstream raw materials:

(2R,3R,4R,5S)-6-Cyclohexyl-3,4-dihydroxy-5-{(S)-3-(1H-imidazol-4-yl)-2-[2-(naphthalen-1-yloxy)-acetylamino]-propionylamino}-2-isobutyl-hexanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide