L-Idonamide, 6-cyclohexyl-2,5,6-trideoxy-5-((2-((hydroxyacetyl)amino)-3-(1H-imidazol-4-yl)-1-oxopropyl)amino)-2-(1-methylethyl)-N-(2-methyl-1-(((2-pyridinylmethyl)amino)carbonyl)butyl)-, (1(1S,2S),5(S))-

Base Information

• Chemical Name: L-Idonamide, 6-cyclohexyl-2,5,6-trideoxy-5-((2-((hydroxyacetyl)amino)-3-(1H-imidazol-4-yl)-1-oxopropyl)amino)-2-(1-methylethyl)-N-(2-methyl-1-(((2-pyridinylmethyl)amino)carbonyl)butyl)-, (1(1S,2S),5(S))-
• CAS No.: 134458-77-8
• Molecular Formula: C₃₅H₅₅N₇O₇
• Molecular Weight: 685.864
• DSSTox Substance ID: DTXSID20158719
• Nikkaji Number: J425.788J
• Wikidata: Q83027034
• ChEMBL ID: CHEMBL3350190

Synonyms:134458-77-8;CHEMBL3350190;Hac-His-Cha-psi(CH(OH)CH(OH))-Val-Ile-Amp;L-Idonamide, 6-cyclohexyl-2,5,6-trideoxy-5-((2-((hydroxyacetyl)amino)-3-(1H-imidazol-4-yl)-1-oxopropyl)amino)-2-(1-methylethyl)-N-(2-methyl-1-(((2-pyridinylmethyl)amino)carbonyl)butyl)-, (1(1S,2S),5(S))-;L-Idonamide, 6-cyclohexyl-2,5,6-trideoxy-5-[[2-[(hydroxyacetyl)amino]-3-(1H-imidazol-4-yl)-1-oxopropyl]amino]-2-(1-methylethyl)-N-[2-methyl-1-[[(2-pyridinylmethyl)amino]carbonyl]butyl]-, [1(1S,2S),5(S)]-;DTXSID20158719;BDBM50229415;Hac-His-Cha-.psi.[CH(OH)CH(OH)]-Val-Ile-Amp;(2R,3R,4R,5S)-6-cyclohexyl-3,4-dihydroxy-5-[[(2S)-2-[(2-hydroxyacetyl)amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-2-isopropyl-N-[(1S,2S)-2-methyl-1-(2-pyridylmethylcarbamoyl)butyl]hexanamide

Chemical Property of L-Idonamide, 6-cyclohexyl-2,5,6-trideoxy-5-((2-((hydroxyacetyl)amino)-3-(1H-imidazol-4-yl)-1-oxopropyl)amino)-2-(1-methylethyl)-N-(2-methyl-1-(((2-pyridinylmethyl)amino)carbonyl)butyl)-, (1(1S,2S),5(S))-

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1093.4°C at 760 mmHg
• Flash Point: 615.1°C
• Density: 1.217g/cm³
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 19
• Exact Mass: 685.41629712
• Heavy Atom Count: 49
• Complexity: 1040

Purity/Quality:

85.0-99.8% ^*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)C(CC3=CN=CN3)NC(=O)CO)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)[C@H](CC3=CN=CN3)NC(=O)CO)O)O)C(C)C

Technology Process of L-Idonamide, 6-cyclohexyl-2,5,6-trideoxy-5-((2-((hydroxyacetyl)amino)-3-(1H-imidazol-4-yl)-1-oxopropyl)amino)-2-(1-methylethyl)-N-(2-methyl-1-(((2-pyridinylmethyl)amino)carbonyl)butyl)-, (1(1S,2S),5(S))-

There total 8 articles about L-Idonamide, 6-cyclohexyl-2,5,6-trideoxy-5-((2-((hydroxyacetyl)amino)-3-(1H-imidazol-4-yl)-1-oxopropyl)amino)-2-(1-methylethyl)-N-(2-methyl-1-(((2-pyridinylmethyl)amino)carbonyl)butyl)-, (1(1S,2S),5(S))- 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:

4-[(S)-2-((1S,2R,3R,4R)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-4-{(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butylcarbamoyl}-hexylcarbamoyl)-2-(2-hydroxy-acetylamino)-ethyl]-imidazole-1-carboxylic acid tert-butyl ester → (2R,3R,4R,5S)-6-Cyclohexyl-3,4-dihydroxy-5-[(S)-2-(2-hydroxy-acetylamino)-3-(1H-imidazol-4-yl)-propionylamino]-2-isopropyl-hexanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide (134458-77-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.25h;

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)-6-Cyclohexyl-3,4-dihydroxy-5-[(S)-2-(2-hydroxy-acetylamino)-3-(1H-imidazol-4-yl)-propionylamino]-2-isopropyl-hexanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide (134458-77-8)

Guidance literature:

Multi-step reaction with 7 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

7: trifluoroacetic acid / CH₂Cl₂ / 0.25 h

With ethandithiol; ruthenium trichloride; diethylphosphoryl cyanide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; periodic acid; N-ethyl-N,N-diisopropylamine; acetyl chloride; trifluoroacetic acid; 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-3,4-dihydroxy-5-[(S)-2-(2-hydroxy-acetylamino)-3-(1H-imidazol-4-yl)-propionylamino]-2-isopropyl-hexanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide (134458-77-8)

Guidance literature:

Multi-step reaction with 7 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

7: trifluoroacetic acid / CH₂Cl₂ / 0.25 h

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

DOI:10.1021/jm00112a005

upstream raw materials:

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

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

1(R)-<3-(tert-butyloxycarbonyl)-4(S)-(cyclohexylmethyl)-2,2-dimethyl-5(R)-oxazolidinyl>-2(S)-isopropyl-1,3-propanediol

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