18-Deoxynargenicin A1

Base Information

• Chemical Name: 18-Deoxynargenicin A1
• CAS No.: 81482-43-1
• Molecular Formula: C₂₈H₃₇NO₇
• Molecular Weight: 499.604
• Mol file: 81482-43-1.mol

Synonyms:18-deoxynargenicin A1

Chemical Property of 18-Deoxynargenicin A1

Chemical Property:

• Vapor Pressure: 7.5E-20mmHg at 25°C
• Boiling Point: 687.6°C at 760 mmHg
• Flash Point: 369.6°C
• PSA: 107.08000
• Density: 1.26g/cm³
• LogP: 3.42960
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 499.25700252
• Heavy Atom Count: 36
• Complexity: 933

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(C=C(C23C(CC(C(=O)O1)OC)C=CC4C2C(C(C(C4O3)OC(=O)C5=CC=CN5)C)O)C)C
• Isomeric SMILES: CC[C@@H]1[C@@H](/C=C(\C23[C@@H](C[C@@H](C(=O)O1)OC)C=C[C@@H]4[C@H]2[C@@H]([C@H]([C@H]([C@@H]4O3)OC(=O)C5=CC=CN5)C)O)/C)C

Technology Process of 18-Deoxynargenicin A1

There total 13 articles about 18-Deoxynargenicin A1 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: 32.0%

C23H34O6 (92080-60-9) + pyrrole-2-carboxyl acid (634-97-9) → 18-deoxynargenicin A1 (81482-43-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 25 ℃;

DOI:10.1021/ja00220a055

Reference yield:

(Z)-(4S,5S)-2-Iodo-5-methoxymethoxy-4-methyl-hept-2-ene (114596-57-5) → 18-deoxynargenicin A1 (81482-43-1)

Guidance literature:

Multi-step reaction with 10 steps

1: -78 - 0 °C

2: EtN(i-Pr)2 / CH₂Cl₂ / 25 °C

3: 39 percent / CrO₃-3,5-dimethylpyrazole / CH₂Cl₂ / -20 °C

4: 1.) (Me₂N)2POCl; 2.) Li, NH₃ / 1.) THF, -78 deg C; 2.) THF, -30 to 0 deg C

5: 1.) 0.01M HCl; 2.) CrO₃ / 1.) H₂O-THF, 25 deg C; 2.) H₂O-acetone, -20 deg C

6: diethyl ether / 0 °C

7: 1.) Mo₅-pyridine-HMPA; 2.) Ag₂O / 1.) THF, -78 deg C; 2.) DMF 25 deg C

8: 1 M HCl / methanol; H₂O / 50 °C

9: 20 percent / (pyridine-S-)2, Ph₃P, / xylene / 140 °C

10: 32 percent / DCC, DMAP / tetrahydrofuran / 25 °C

With chromium(VI) oxide; hydrogenchloride; dmap; (pyridine-S-)2; Mo₅-pyridine-HMPA; ammonia; lithium; N,N,N',N'-Tetramethylphosphorodiamidic chloride; CrO₃-3.5-dimethylpyrazole; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; xylene;

DOI:10.1021/ja00220a055

Reference yield:

(1aR,2R,3R,3aS,7aR,7bS)-3-Methoxymethoxy-2-methyl-1a,3,3a,7,7a,7b-hexahydro-2H-1-oxa-cyclopropa[a]naphthalen-4-one (92775-46-7,114673-13-1,142034-10-4) → 18-deoxynargenicin A1 (81482-43-1)

Guidance literature:

Multi-step reaction with 10 steps

1: -78 - 0 °C

2: EtN(i-Pr)2 / CH₂Cl₂ / 25 °C

3: 39 percent / CrO₃-3,5-dimethylpyrazole / CH₂Cl₂ / -20 °C

4: 1.) (Me₂N)2POCl; 2.) Li, NH₃ / 1.) THF, -78 deg C; 2.) THF, -30 to 0 deg C

5: 1.) 0.01M HCl; 2.) CrO₃ / 1.) H₂O-THF, 25 deg C; 2.) H₂O-acetone, -20 deg C

6: diethyl ether / 0 °C

7: 1.) Mo₅-pyridine-HMPA; 2.) Ag₂O / 1.) THF, -78 deg C; 2.) DMF 25 deg C

8: 1 M HCl / methanol; H₂O / 50 °C

9: 20 percent / (pyridine-S-)2, Ph₃P, / xylene / 140 °C

10: 32 percent / DCC, DMAP / tetrahydrofuran / 25 °C

With chromium(VI) oxide; hydrogenchloride; dmap; (pyridine-S-)2; Mo₅-pyridine-HMPA; ammonia; lithium; N,N,N',N'-Tetramethylphosphorodiamidic chloride; CrO₃-3.5-dimethylpyrazole; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; xylene;

DOI:10.1021/ja00220a055

upstream raw materials:

C₂₃H₃₄O₆

pyrrole-2-carboxyl acid

(Z)-(4S,5S)-2-Iodo-5-methoxymethoxy-4-methyl-hept-2-ene

(1aR,2R,3R,3aS,7aR,7bS)-3-Methoxymethoxy-2-methyl-1a,3,3a,7,7a,7b-hexahydro-2H-1-oxa-cyclopropa[a]naphthalen-4-one