acetylaranotin

Base Information

• Chemical Name: acetylaranotin
• CAS No.: 20485-01-2
• Molecular Formula: C₂₂H₂₀N₂O₈S₂
• Molecular Weight: 504.541
• Mol file: 20485-01-2.mol

Synonyms:8H,16H-7a,15a-Epidithio-7H,15H-bisoxepino[3',4':4,5]pyrrolo[1,2-a:1',2'-d]pyrazine-7,15-dione,5,13-bis(acetyloxy)-5,5a,13,13a-tetrahydro-, [5S-(5a,5aa,7ab,13a,13aa,15ab)]-;8H,16H-7a,15a-Epidithio-7H,15H-bisoxepino[3',4':4,5]pyrrolo[1,2-a:1',2'-d]pyrazine-7,15-dione,5,5a,13,13a-tetrahydro-5,13-dihydroxy-, diacetate (ester) (8CI);Acetylaranotin; Antibiotic A 21101-II; Aranotin, acetyl-; LL-S 88a

Chemical Property of acetylaranotin

Chemical Property:

• Boiling Point: 814.8°Cat760mmHg
• Flash Point: 446.6°C
• PSA: 162.28000
• Density: 1.65g/cm³
• LogP: 1.58420

Purity/Quality:

ACETYLARANOTIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of acetylaranotin

There total 35 articles about acetylaranotin 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: 45.0%

(7aR)-5t,13t-diacetoxy-(5at,13at)-5,5a,13,13a-tetrahydro-8H,16H-7ar,15ac-epitetrasulfano-bis(oxepino[3',4':4,5]pyrrolo)[1,2-a;1',2'-d]pyrazine-7,15-dione (25825-54-1) → acetylaranotin (20485-01-2)

Guidance literature:

With 1.3-propanedithiol; triethylamine; In dichloromethane; acetonitrile; for 0.333333h; Inert atmosphere;

DOI:10.1021/ja209354e

Reference yield:

(5aS)-5c,13c-diacetoxy-7a,15a-dimercapto-(5ar,7at,13ac,15at)-5,5a,7a,8,13,13a,15a,16-octahydro-bis(oxepino[3',4':4,5]pyrrolo)[1,2-a;1',2'-d]pyrazine-7,15-dione (25825-51-8) → acetylaranotin (20485-01-2)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane;

DOI:10.1021/jm00254a010

Reference yield:

C20H27NO4 (1343480-94-3) → acetylaranotin (20485-01-2)

Guidance literature:

Multi-step reaction with 18 steps

1.1: triethylsilane / dichloromethane / Inert atmosphere

2.1: triethylamine / 1,4-dioxane; water

3.1: oxygen; ozone / dichloromethane / -78 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: tetrahydrofuran / 0.42 h / -78 - 0 °C / Inert atmosphere

4.2: 0.17 h / 0 °C / Inert atmosphere

4.3: 0 - 20 °C / Inert atmosphere

5.1: sodium tetrahydroborate / ethanol / 1.75 h / Inert atmosphere

6.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

7.1: acetic acid / tetrahydrofuran; water / 6 h / Inert atmosphere

8.1: pyridine; Dess-Martin periodane / dichloromethane / 3.5 h / Inert atmosphere

9.1: N-chloro-succinimide; pyrrolidinium 2,2,2-trifluoroacetate / dichloromethane / 30 h

10.1: sodium tetrahydroborate / ethanol / 1.5 h / Inert atmosphere

11.1: chloro(1,5-cyclooctadiene)rhodium(I) dimer; P(p-C₆H₄F)3 / N,N-dimethyl-formamide / 26 h / 85 °C / Inert atmosphere

12.1: lithium carbonate; lithium chloride / N,N-dimethyl-formamide / 75 h / 100 °C / Inert atmosphere

13.1: trimethyltin(IV) hydroxide / 1,2-dichloro-ethane / 30 h / 80 °C / Inert atmosphere

14.1: bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine / dichloromethane / 24 h / Inert atmosphere

15.1: tetrabutylammonium tetra(tert-butyl alcohol) coordinate fluoride / acetonitrile / 2.33 h / 70 °C / Inert atmosphere

16.1: sulfur; sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.88 h / Inert atmosphere

17.1: dmap / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

18.1: 1.3-propanedithiol; triethylamine / dichloromethane; acetonitrile / 0.33 h / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; 1.3-propanedithiol; triethylsilane; sulfur; dmap; sodium tetrahydroborate; N-chloro-succinimide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; tetrabutylammonium tetra(tert-butyl alcohol) coordinate fluoride; oxygen; sodium hexamethyldisilazane; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; lithium carbonate; pyrrolidinium 2,2,2-trifluoroacetate; Dess-Martin periodane; ozone; acetic acid; triethylamine; trimethyltin(IV) hydroxide; lithium chloride; P(p-C₆H₄F)3; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 4.2: Mitsunobu reaction / 4.3: Mitsunobu reaction;

DOI:10.1021/ja209354e

upstream raw materials:

aranotin

(5aS)-5c,13c-diacetoxy-7a,15a-dimercapto-(5ar,7at,13ac,15at)-5,5a,7a,8,13,13a,15a,16-octahydro-bis(oxepino[3',4':4,5]pyrrolo)[1,2-a;1',2'-d]pyrazine-7,15-dione

(5S,5aS,7aS,13S,13aS,15aS)-5,13-dihydroxy-5,5a,7a,8,13,13a,15a,16-octahydrooxepino[3',4':4,5]pyrrolo[1,2-a]oxepino[3',4':4,5]pyrrolo[1,2-d]pyrazine-7,15-dione

C₁₇H₂₉NO₆Si

Refernces

• 1、 Murdock. "Antiviral agents. Chemical modifications of a disulfide antibiotic, acetylaranotin". . p. 827 - 835. Retrieved 1974.
• 2、 Fujiwara, Hideto,Kurogi, Taichi,Okaya, Shun,Okano, Kentaro,Tokuyama, Hidetoshi. "Total synthesis of (-)-Acetylaranotin". . p. 13062 - 13065. Retrieved 2013/02/26.