N~2~-(8-{[16-(Acetyloxy)-14-hydroxy-17-(2-oxo-2H-pyran-4-yl)androstan-3-yl]oxy}-1-hydroxy-8-oxooctylidene)arginine

Base Information

• Chemical Name: N~2~-(8-{[16-(Acetyloxy)-14-hydroxy-17-(2-oxo-2H-pyran-4-yl)androstan-3-yl]oxy}-1-hydroxy-8-oxooctylidene)arginine
• CAS No.: 464-81-3
• Molecular Formula: C40H60 N4 O10
• Molecular Weight: 756.937
• DSSTox Substance ID: DTXSID20963567
• Wikidata: Q82945453
• Mol file: 464-81-3.mol

Synonyms:DTXSID20963567;N~2~-(8-{[16-(Acetyloxy)-14-hydroxy-17-(2-oxo-2H-pyran-4-yl)androstan-3-yl]oxy}-1-hydroxy-8-oxooctylidene)arginine

Chemical Property of N~2~-(8-{[16-(Acetyloxy)-14-hydroxy-17-(2-oxo-2H-pyran-4-yl)androstan-3-yl]oxy}-1-hydroxy-8-oxooctylidene)arginine

Chemical Property:

• PSA: 231.34000
• LogP: 6.08950
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 18
• Exact Mass: 756.43094412
• Heavy Atom Count: 54
• Complexity: 1530

Purity/Quality:

98% ^*data from raw suppliers

BUFOTOXIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC1CC2(C3CCC4CC(CCC4(C3CCC2(C1C5=CC(=O)OC=C5)C)C)OC(=O)CCCCCCC(=O)NC(CCCN=C(N)N)C(=O)O)O
• Isomeric SMILES: CC(=O)O[C@H]1C[C@@]2(C3CC[C@@H]4C[C@H](CC[C@@]4(C3CC[C@@]2([C@H]1C5=CC(=O)OC=C5)C)C)OC(=O)CCCCCCC(=O)NC(CCCN=C(N)N)C(=O)O)O

Technology Process of N~2~-(8-{[16-(Acetyloxy)-14-hydroxy-17-(2-oxo-2H-pyran-4-yl)androstan-3-yl]oxy}-1-hydroxy-8-oxooctylidene)arginine

There total 1 articles about N~2~-(8-{[16-(Acetyloxy)-14-hydroxy-17-(2-oxo-2H-pyran-4-yl)androstan-3-yl]oxy}-1-hydroxy-8-oxooctylidene)arginine 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:

Epietiocholanolone (571-31-3) → Bufotoxin (464-81-3)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 15 h / 70 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

3.1: palladium diacetate / dichloromethane; acetonitrile / 25 h / 20 °C / Inert atmosphere

4.1: silica gel; N-ethyl-N,N-diisopropylamine / 4 h / 80 °C / Inert atmosphere

5.1: oxygen; phenylsilane; cobalt(II) aceylacetonate / 1,4-dioxane / 5 h / 20 °C / 760.05 Torr

6.1: triethylamine; hydrazine hydrate / ethanol / 13 h / 50 °C / Inert atmosphere

6.2: 0.67 h / 0 °C

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) chloride; lithium chloride / dimethyl sulfoxide; tetrahydrofuran / 13 h / 60 °C / Inert atmosphere

8.1: 3-chloro-benzenecarboperoxoic acid; sodium carbonate / dichloromethane / 5 h / -78 - -20 °C / Inert atmosphere

9.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere

10.1: methanol; sodium tetrahydroborate / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

11.1: pyridine / 18 h / 20 °C / Inert atmosphere

12.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 124 h / 20 °C / Inert atmosphere

13.1: dmap / dichloromethane / 11 h / 20 °C / Inert atmosphere

14.1: 4-methyl-morpholine / tetrahydrofuran / 0.17 h / -10 °C / Molecular sieve; Inert atmosphere

14.2: 0.5 h / -10 °C / Molecular sieve; Inert atmosphere

14.3: 2 h / 20 °C / Molecular sieve; Inert atmosphere

With 4-methyl-morpholine; pyridine; 1H-imidazole; 2,6-dimethylpyridine; methanol; dmap; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; phenylsilane; oxygen; palladium diacetate; silica gel; sodium carbonate; pyridine hydrogenfluoride; cobalt(II) aceylacetonate; hydrazine hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; copper(l) chloride; lithium chloride; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.orglett.0c03251

Reference yield:

Bufotoxin (464-81-3) → 5?[(3S,5R,8R,9S,10S,13S)?3?hydroxy?10,13?di?methyl?2,3,4,5,6,7,8,9,10,11,12,13?dodecahydro?1H?cyclopenta[a]phenanthren?17?yl]?2H?pyran?2?one (474-53-3)

Guidance literature:

With hydrogenchloride;

upstream raw materials:

Epietiocholanolone

Downstream raw materials:

5?[(3S,5R,8R,9S,10S,13S)?3?hydroxy?10,13?di?methyl?2,3,4,5,6,7,8,9,10,11,12,13?dodecahydro?1H?cyclopenta[a]phenanthren?17?yl]?2H?pyran?2?one

Refernces