Lavendomycin

Base Information

• Chemical Name: Lavendomycin
• CAS No.: 82987-09-5
• Molecular Formula: C₂₉H₅₀N₁₀O₈
• Molecular Weight: 666.778
• Metabolomics Workbench ID: 98393
• Wikidata: Q110186449
• Mol file: 82987-09-5.mol

Synonyms:FR-900201;lavendomycin

Chemical Property of Lavendomycin

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 309.86000
• Density: 1.5g/cm³
• LogP: 1.59700
• XLogP3: -5.5
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 15
• Exact Mass: 666.38130859
• Heavy Atom Count: 47
• Complexity: 1220

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(C(=O)NC(CO)C(=O)O)NC(=O)C1CCCN1C(=O)C2CCCCN2C(=O)C(C(C)N)NC(=O)C(C(C)CCN=C(N)N)N
• Isomeric SMILES: C/C=C(/C(=O)N[C@@H](CO)C(=O)O)\NC(=O)[C@@H]1CCCN1C(=O)[C@@H]2CCCCN2C(=O)[C@H]([C@@H](C)N)NC(=O)[C@H]([C@H](C)CCN=C(N)N)N

Technology Process of Lavendomycin

There total 31 articles about Lavendomycin 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: 79.0%

C61H94N10O16 → (-)-lavendomycin (82987-09-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 2h;

DOI:10.1039/c39900001216

Reference yield:

5-Ethoxy-pent-2-ensaeure-ethylester (13369-27-2) → (-)-lavendomycin (82987-09-5)

Guidance literature:

Multi-step reaction with 18 steps

1: 94 percent / diisobutylaluminium hydride (DiBAH) / CH₂Cl₂ / 3 h / -78 °C

2: 72 percent / t-BuOOH, L(+)-diethyl tartrate, Ti(O-i-Pr)4 / CH₂Cl₂ / 3 h / -20 °C

3: toluene; hexane / 2 h / Ambient temperature

4: 53 percent / pyridine, dimethylaminopyridine (DMAP) / CH₂Cl₂ / 8 h / 0 - 20 °C

5: 93 percent / HN₃, PPh₃, DEAD / toluene / 2 h / Ambient temperature

6: H₂ / Pd / methanol / 5 h / Ambient temperature

7: KOH / toluene / 4 h / 0 °C

8: 77 percent / BBr₃ / CH₂Cl₂ / 3 h / 20 - 50 °C

9: 84 percent / NaN₃ / dimethylformamide / 16 h / 140 °C

10: 87 percent / DMAP, Et₃N / CH₂Cl₂ / 12 h / Ambient temperature

11: 78 percent / CsCO₃ / methanol / 14 h / Ambient temperature

12: 81 percent / pyridinium dichromate (PDC) / dimethylformamide / 12 h / Ambient temperature

13: 82 percent / H₂ / Pd / methanol / 5 h / Ambient temperature

14: 67 percent / K₂CO₃ / 14 h / Ambient temperature

15: 73 percent / NaOH / dioxane / 12 h / 0 - 20 °C

16: 41 percent / benzotriazole-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), Et₃N / CH₂Cl₂ / 12 h / Ambient temperature

17: 90 percent / Pd(PPh₃)4, morpholine / tetrahydrofuran / 1 h / Ambient temperature

18: 79 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h

With morpholine; pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; potassium hydroxide; sodium hydroxide; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; diethyl (2R,3R)-tartrate; tris-(2-chloro-ethyl)-amine; hydrogen; boron tribromide; diisobutylaluminium hydride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1039/c39900001216

Reference yield:

(2R,3R)-5-Ethoxy-3-methyl-pentane-1,2-diol (131669-46-0) → (-)-lavendomycin (82987-09-5)

Guidance literature:

Multi-step reaction with 15 steps

1: 53 percent / pyridine, dimethylaminopyridine (DMAP) / CH₂Cl₂ / 8 h / 0 - 20 °C

2: 93 percent / HN₃, PPh₃, DEAD / toluene / 2 h / Ambient temperature

3: H₂ / Pd / methanol / 5 h / Ambient temperature

4: KOH / toluene / 4 h / 0 °C

5: 77 percent / BBr₃ / CH₂Cl₂ / 3 h / 20 - 50 °C

6: 84 percent / NaN₃ / dimethylformamide / 16 h / 140 °C

7: 87 percent / DMAP, Et₃N / CH₂Cl₂ / 12 h / Ambient temperature

8: 78 percent / CsCO₃ / methanol / 14 h / Ambient temperature

9: 81 percent / pyridinium dichromate (PDC) / dimethylformamide / 12 h / Ambient temperature

10: 82 percent / H₂ / Pd / methanol / 5 h / Ambient temperature

11: 67 percent / K₂CO₃ / 14 h / Ambient temperature

12: 73 percent / NaOH / dioxane / 12 h / 0 - 20 °C

13: 41 percent / benzotriazole-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), Et₃N / CH₂Cl₂ / 12 h / Ambient temperature

14: 90 percent / Pd(PPh₃)4, morpholine / tetrahydrofuran / 1 h / Ambient temperature

15: 79 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h

With morpholine; pyridine; dmap; potassium hydroxide; sodium hydroxide; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; tris-(2-chloro-ethyl)-amine; hydrogen; boron tribromide; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1039/c39900001216

upstream raw materials:

5-Ethoxy-pent-2-ensaeure-ethylester

C₆₄H₉₈N₁₀O₁₆

(2R,3R)-5-Ethoxy-3-methyl-pentane-1,2-diol

[(2R,3R)-3-(2-Ethoxy-ethyl)-oxiranyl]-methanol

Refernces