Cyanustine

Base Information

• Chemical Name: Cyanustine
• CAS No.: 17958-39-3
• Deprecated CAS: 34081-99-7
• Molecular Formula: C15H25NO4•ClH
• Molecular Weight: 319.87

Synonyms:Cyanustine;(+)-Cyanustine;Cynaustine hydrochloride;Cynaustine;17958-39-3;[(8R)-3,4,5,6,7,8-hexahydropyrrolizin-4-ium-1-yl]methyl (2R)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate;chloride;Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl ester, hydrochloride, (7aR-(7(2S*,3S*),7aR*))-;C15-H25-N-O4.Cl-H;C15H25NO4.ClH;AKOS040735532;LS-46254;Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl ester, (7aR-(7(2S*,3S*),7aR*))-

Chemical Property of Cyanustine

Chemical Property:

• Vapor Pressure: 1.09E-08mmHg at 25°C
• Boiling Point: 416.8°C at 760 mmHg
• Flash Point: 205.9°C
• PSA: 70.00000
• LogP: 1.44180
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 319.1550360
• Heavy Atom Count: 21
• Complexity: 407

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: A poison.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(C)O)(C(=O)OCC1=CC[NH+]2C1CCC2)O.[Cl-]
• Isomeric SMILES: C[C@@H]([C@](C(C)C)(C(=O)OCC1=CC[NH+]2[C@@H]1CCC2)O)O.[Cl-]

Technology Process of Cyanustine

There total 12 articles about Cyanustine 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: 37.0%

(4S,5S)-((S)-2-(2-(1,3-dioxan-2-yl)ethyl)-1-((S)-tert-butylsulfinyl)-2,5-dihydro-1H-pyrrol-3-yl)methyl 4-isopropyl-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate (1369385-54-5) → Amabiline (551-58-6,17958-39-3,17958-43-9,84471-36-3,85798-06-7,92593-89-0)

Guidance literature:

(4S,5S)-((S)-2-(2-(1,3-dioxan-2-yl)ethyl)-1-((S)-tert-butylsulfinyl)-2,5-dihydro-1H-pyrrol-3-yl)methyl 4-isopropyl-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate; With trifluoroacetic acid; In water; at 20 ℃; for 1.5h; Inert atmosphere;

In 1,2-dichloro-ethane; at 20 ℃; for 16h;

In dichloromethane; for 12h;

DOI:10.1021/ol300466a

Reference yield:

(S)-N-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(1,3-dioxan-2-yl)pent-1-en-3-yl)-2-methylpropane-2-sulfinamide (1369385-45-4) → Amabiline (551-58-6,17958-39-3,17958-43-9,84471-36-3,85798-06-7,92593-89-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.33 h / -20 °C

1.2: 1 h / -20 °C

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 16 h / 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

5.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

5.2: 1.5 h / 20 °C / Inert atmosphere

6.1: trifluoroacetic acid / water / 1.5 h / 20 °C / Inert atmosphere

6.2: MP-BH(OAc)3 / 16 h / 20 °C

6.3: PS-carbonate / 12 h

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ol300466a

Reference yield:

(S)-N-allyl-N-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(1,3-dioxan-2-yl)pent-1-en-3-yl)-2-methylpropane-2-sulfinamide (1369385-47-6) → Amabiline (551-58-6,17958-39-3,17958-43-9,84471-36-3,85798-06-7,92593-89-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 16 h / 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

4.2: 1.5 h / 20 °C / Inert atmosphere

5.1: trifluoroacetic acid / water / 1.5 h / 20 °C / Inert atmosphere

5.2: MP-BH(OAc)3 / 16 h / 20 °C

5.3: PS-carbonate / 12 h

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ol300466a

upstream raw materials:

(S)-N-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(1,3-dioxan-2-yl)pent-1-en-3-yl)-2-methylpropane-2-sulfinamide

(S)-N-allyl-N-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(1,3-dioxan-2-yl)pent-1-en-3-yl)-2-methylpropane-2-sulfinamide

(S)-2-(2-(1,3-dioxan-2-yl)ethyl)-3-(((tert-butyldimethylsilyl)oxy)methyl)-1-((S)-tertbutylsulfinyl)-2,5-dihydro-1H-pyrrole

((S)-2-(2-(1,3-dioxan-2-yl)ethyl)-1-((S)-tert-butylsulfinyl)-2,5-dihydro-1H-pyrrol-3-yl)methanol

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