L-Idonamide, 6-cyclohexyl-5-((cyclohexylacetyl)amino)-2,5,6-trideoxy-2-(1-methylethyl)-N-(2-methyl-1-(((2-pyridinylmethyl)amino)carbonyl)butyl)-, (S-(R*,R*))-

Base Information

• Chemical Name: L-Idonamide, 6-cyclohexyl-5-((cyclohexylacetyl)amino)-2,5,6-trideoxy-2-(1-methylethyl)-N-(2-methyl-1-(((2-pyridinylmethyl)amino)carbonyl)butyl)-, (S-(R*,R*))-
• CAS No.: 134458-79-0
• Molecular Formula: C₃₅H₅₈N₄O₅
• Molecular Weight: 614.869
• DSSTox Substance ID: DTXSID90158721
• Wikidata: Q83027038
• ChEMBL ID: CHEMBL3085447

Synonyms:134458-79-0;Cha-Cha-psi(CH(OH)CH(OH))-Val-Ile-Amp;L-Idonamide, 6-cyclohexyl-5-((cyclohexylacetyl)amino)-2,5,6-trideoxy-2-(1-methylethyl)-N-(2-methyl-1-(((2-pyridinylmethyl)amino)carbonyl)butyl)-, (S-(R*,R*))-;CHEMBL3085447;L-Idonamide, 6-cyclohexyl-5-[(cyclohexylacetyl)amino]-2,5,6-trideoxy-2-(1-methylethyl)-N-[2-methyl-1-[[(2-pyridinylmethyl)amino]carbonyl]butyl]-, [S-(R*,R*)]-;DTXSID90158721;BDBM50453058;Cha-Cha-.psi.[CH(OH)CH(OH)]-Val-Ile-Amp;(2R,3R,4R,5S)-6-cyclohexyl-5-[(2-cyclohexylacetyl)amino]-3,4-dihydroxy-2-isopropyl-N-[(1S,2S)-2-methyl-1-(2-pyridylmethylcarbamoyl)butyl]hexanamide

Chemical Property of L-Idonamide, 6-cyclohexyl-5-((cyclohexylacetyl)amino)-2,5,6-trideoxy-2-(1-methylethyl)-N-(2-methyl-1-(((2-pyridinylmethyl)amino)carbonyl)butyl)-, (S-(R*,R*))-

Chemical Property:

• Vapor Pressure: 1.68E-33mmHg at 25°C
• Boiling Point: 884.1°C at 760 mmHg
• Flash Point: 488.5°C
• Density: 1.097g/cm³
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 16
• Exact Mass: 614.44072096
• Heavy Atom Count: 44
• Complexity: 873

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)NCC1=CC=CC=N1)NC(=O)C(C(C)C)C(C(C(CC2CCCCC2)NC(=O)CC3CCCCC3)O)O
• Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)NCC1=CC=CC=N1)NC(=O)[C@@H]([C@H]([C@@H]([C@H](CC2CCCCC2)NC(=O)CC3CCCCC3)O)O)C(C)C

Technology Process of L-Idonamide, 6-cyclohexyl-5-((cyclohexylacetyl)amino)-2,5,6-trideoxy-2-(1-methylethyl)-N-(2-methyl-1-(((2-pyridinylmethyl)amino)carbonyl)butyl)-, (S-(R*,R*))-

There total 7 articles about L-Idonamide, 6-cyclohexyl-5-((cyclohexylacetyl)amino)-2,5,6-trideoxy-2-(1-methylethyl)-N-(2-methyl-1-(((2-pyridinylmethyl)amino)carbonyl)butyl)-, (S-(R*,R*))- 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:

tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (117997-58-7) → (2R,3R,4R,5S)-6-Cyclohexyl-5-(2-cyclohexyl-acetylamino)-3,4-dihydroxy-2-isopropyl-hexanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide (134458-79-0)

Guidance literature:

Multi-step reaction with 6 steps

3: 98 percent / periodic acid, ruthenium trichloride hydrate / acetonitrile; CCl₄; H₂O / 2 h

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

5: acetyl chloride, ethanedithiol / methanol / 5 h

6: diisopropylethylamine, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / CH₂Cl₂ / 14 h

With ethandithiol; ruthenium trichloride; diethylphosphoryl cyanide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; periodic acid; N-ethyl-N,N-diisopropylamine; acetyl chloride; In methanol; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/jm00112a005

Reference yield:

(4R,5S)-(+)-3-[3-methyl-1-oxobut-1-yl]-4-methyl-5-phenyl-2-oxazolidinone (107599-99-5) → (2R,3R,4R,5S)-6-Cyclohexyl-5-(2-cyclohexyl-acetylamino)-3,4-dihydroxy-2-isopropyl-hexanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide (134458-79-0)

Guidance literature:

Multi-step reaction with 6 steps

3: 98 percent / periodic acid, ruthenium trichloride hydrate / acetonitrile; CCl₄; H₂O / 2 h

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

5: acetyl chloride, ethanedithiol / methanol / 5 h

6: diisopropylethylamine, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / CH₂Cl₂ / 14 h

With ethandithiol; ruthenium trichloride; diethylphosphoryl cyanide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; periodic acid; N-ethyl-N,N-diisopropylamine; acetyl chloride; In methanol; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/jm00112a005

Reference yield:

3-<3(R)-<3-(tert-butyloxycarbonyl)-4(S)-cyclohexylmethyl)-2,2-dimethyl-5(R)-oxazolidinyl>-3-hydroxy-2(R)-isopropyl-1-oxopropyl>-4(R)-methyl-5(S)-phenyl-2-oxazolidinone (112190-42-8) → (2R,3R,4R,5S)-6-Cyclohexyl-5-(2-cyclohexyl-acetylamino)-3,4-dihydroxy-2-isopropyl-hexanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide (134458-79-0)

Guidance literature:

Multi-step reaction with 5 steps

2: 98 percent / periodic acid, ruthenium trichloride hydrate / acetonitrile; CCl₄; H₂O / 2 h

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

4: acetyl chloride, ethanedithiol / methanol / 5 h

5: diisopropylethylamine, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / CH₂Cl₂ / 14 h

With ethandithiol; ruthenium trichloride; diethylphosphoryl cyanide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; periodic acid; N-ethyl-N,N-diisopropylamine; acetyl chloride; In methanol; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/jm00112a005

upstream raw materials:

Cyclohexylacetic acid

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

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

(4R,5S)-(+)-3-[3-methyl-1-oxobut-1-yl]-4-methyl-5-phenyl-2-oxazolidinone

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