Acetylstrophanthidin

Base Information

• Chemical Name: Acetylstrophanthidin
• CAS No.: 60-38-8
• Molecular Formula: C25H34O7
• Molecular Weight: 446.541
• European Community (EC) Number: 200-474-0
• NSC Number: 92954
• UNII: JG33H36364
• DSSTox Substance ID: DTXSID401018935
• Nikkaji Number: J14.349I
• Wikidata: Q27126403
• Metabolomics Workbench ID: 60357
• ChEMBL ID: CHEMBL1981679
• Mol file: 60-38-8.mol

Synonyms:acetylstrophanthidin;acetylstrophantindin

Chemical Property of Acetylstrophanthidin

Chemical Property:

• Melting Point: 246-248℃
• Boiling Point: 612.8 °C at 760 mmHg
• Flash Point: 205.7 °C
• PSA: 110.13000
• Density: 1.31 g/cm³
• LogP: 2.46900
• Storage Temp.: −20°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 446.23045342
• Heavy Atom Count: 32
• Complexity: 882

Purity/Quality:

99% ^*data from raw suppliers

Acetylstrophanthidin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CCC2(C3CCC4(C(CCC4(C3CCC2(C1)O)O)C5=CC(=O)OC5)C)C=O
• Isomeric SMILES: CC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@@]4([C@H](CC[C@@]4([C@@H]3CC[C@@]2(C1)O)O)C5=CC(=O)OC5)C)C=O
• Uses: Acetylstrophanthidin is a cardiac glycoside with biphasic effect.

Technology Process of Acetylstrophanthidin

There total 21 articles about Acetylstrophanthidin 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:

strophanthidol 3β-acetate (4947-61-9) → strophanthidin acetate (60-38-8)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In water; acetone; at 0 ℃;

DOI:10.1016/S0040-4039(01)80714-0

Reference yield:

16-dehydropregnenolone acetate (979-02-2) → strophanthidin acetate (60-38-8)

Guidance literature:

Multi-step reaction with 15 steps

1: CH₃CONHBr, HClO₄ / H₂O; diethyl ether / Ambient temperature

2: 83 percent / (AcO)4Pb, I₂, CaCO₃ / benzene / Heating

3: NBS, AIBN / CCl₄ / Heating

4: LiI, Li₂CO₃ / dimethylformamide / 100 °C

5: 68 percent / Ph₂SiH₂, ZnCl₂ / (dppe)2Pd / CHCl₃

6: BF₃*Et₂O / methanol / Ambient temperature

7: KHCO₃ / benzene; methanol; H₂O

8: DCC / DMAP / diethyl ether; pyridine / Ambient temperature

9: 81 percent / t-BuOK / tetrahydrofuran / Ambient temperature

10: Zn / acetic acid; methanol / 80 °C

11: 86 percent / 70 °C

12: CH₃CONHBr, HClO₄ / H₂O; dioxane / Ambient temperature

13: Bu₃SnH, AIBN / benzene / Heating

14: KHCO₃ / benzene; methanol; H₂O

15: CrO₃, H₂SO₄ / acetone; H₂O / 0 °C

With chromium(VI) oxide; lead(IV) acetate; N-Bromosuccinimide; perchloric acid; 2,2'-azobis(isobutyronitrile); sulfuric acid; boron trifluoride diethyl etherate; diphenylsilane; potassium tert-butylate; iodine; tri-n-butyl-tin hydride; lithium carbonate; potassium hydrogencarbonate; dicyclohexyl-carbodiimide; calcium carbonate; zinc(II) chloride; lithium iodide; zinc; N-bromoacetamide; dmap; bis[1,2-bis(diphenylphosphino)ethane]palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; tetrachloromethane; diethyl ether; chloroform; water; acetic acid; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/S0040-4039(01)80714-0

Reference yield:

Acetic acid (3S,5R,6R,8S,9S,10R,13S,14S)-17-acetyl-5-bromo-6-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester (125139-77-7) → strophanthidin acetate (60-38-8)

Guidance literature:

Multi-step reaction with 14 steps

1: 83 percent / (AcO)4Pb, I₂, CaCO₃ / benzene / Heating

2: NBS, AIBN / CCl₄ / Heating

3: LiI, Li₂CO₃ / dimethylformamide / 100 °C

4: 68 percent / Ph₂SiH₂, ZnCl₂ / (dppe)2Pd / CHCl₃

5: BF₃*Et₂O / methanol / Ambient temperature

6: KHCO₃ / benzene; methanol; H₂O

7: DCC / DMAP / diethyl ether; pyridine / Ambient temperature

8: 81 percent / t-BuOK / tetrahydrofuran / Ambient temperature

9: Zn / acetic acid; methanol / 80 °C

10: 86 percent / 70 °C

11: CH₃CONHBr, HClO₄ / H₂O; dioxane / Ambient temperature

12: Bu₃SnH, AIBN / benzene / Heating

13: KHCO₃ / benzene; methanol; H₂O

14: CrO₃, H₂SO₄ / acetone; H₂O / 0 °C

With chromium(VI) oxide; lead(IV) acetate; N-Bromosuccinimide; perchloric acid; 2,2'-azobis(isobutyronitrile); sulfuric acid; boron trifluoride diethyl etherate; diphenylsilane; potassium tert-butylate; iodine; tri-n-butyl-tin hydride; lithium carbonate; potassium hydrogencarbonate; dicyclohexyl-carbodiimide; calcium carbonate; zinc(II) chloride; lithium iodide; zinc; N-bromoacetamide; dmap; bis[1,2-bis(diphenylphosphino)ethane]palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; tetrachloromethane; diethyl ether; chloroform; water; acetic acid; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/S0040-4039(01)80714-0

upstream raw materials:

acetic anhydride

strophanthidin

strophanthidol 3β-acetate

16-dehydropregnenolone acetate