C₁₇H₂₀(OH)2(OCOCH₃)2(CH₂OCOCH₃)(CH₃)(OCOC₆H₄OCH₃)(CHCH₂)

Base Information

• Chemical Name: C₁₇H₂₀(OH)2(OCOCH₃)2(CH₂OCOCH₃)(CH₃)(OCOC₆H₄OCH₃)(CHCH₂)
• CAS No.: 1018988-55-0
• Molecular Formula: C₃₅H₄₆O₁₁
• Molecular Weight: 642.744
• Mol file: 1018988-55-0.mol

Synonyms:C₁₇H₂₀(OH)2(OCOCH₃)2(CH₂OCOCH₃)(CH₃)(OCOC₆H₄OCH₃)(CHCH₂)

Chemical Property of C₁₇H₂₀(OH)2(OCOCH₃)2(CH₂OCOCH₃)(CH₃)(OCOC₆H₄OCH₃)(CHCH₂)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₁₇H₂₀(OH)2(OCOCH₃)2(CH₂OCOCH₃)(CH₃)(OCOC₆H₄OCH₃)(CHCH₂)

There total 17 articles about C₁₇H₂₀(OH)2(OCOCH₃)2(CH₂OCOCH₃)(CH₃)(OCOC₆H₄OCH₃)(CHCH₂) 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: 67.0%

C34H44O12 (1018988-54-9) + diazomethyl-trimethyl-silane (18107-18-1) → C17H20(OH)2(OCOCH3)2(CH2OCOCH3)(CH3)(OCOC6H4OCH3)(CHCH2) (1018988-55-0)

Guidance literature:

With triphenylphosphine; Wilkinson's catalyst; In tetrahydrofuran; isopropyl alcohol; at 20 ℃; for 16h;

DOI:10.1002/anie.200704959

Reference yield:

C58H78O7Si3 (1018988-60-7) → C17H20(OH)2(OCOCH3)2(CH2OCOCH3)(CH3)(OCOC6H4OCH3)(CHCH2) (1018988-55-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 2,6-di-tert-butyl-4-methylpyridine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetonitrile / 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / -40 - -30 °C / Inert atmosphere

3.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 13 °C / Inert atmosphere

4.1: lithium borohydride / tetrahydrofuran / Inert atmosphere; Reflux

4.2: 4 h / 20 °C / Inert atmosphere

5.1: lithium borohydride / tetrahydrofuran / 26.5 h / 20 °C / Inert atmosphere; Reflux

5.2: 4 h / 20 °C / Inert atmosphere

6.1: water; acetic acid / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

7.1: dmap / pyridine; dichloromethane / 24 h / 20 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

9.1: peracetic acid; mercury(II) diacetate; acetic acid / 4 h / 20 °C / Inert atmosphere

10.1: 1H-imidazole / dichloromethane / 4 h / 0 °C / Inert atmosphere

11.1: dmap / pyridine; dichloromethane / 0 - 40 °C / Inert atmosphere

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

13.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

14.1: Wilkinson's catalyst; triphenylphosphine; isopropyl alcohol / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

With 1H-imidazole; peracetic acid; dmap; sodium tetrahydroborate; Wilkinson's catalyst; lithium borohydride; 2,6-di-tert-butyl-4-methylpyridine; mercury(II) diacetate; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; isopropyl alcohol; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; ethanol; dichloromethane; acetonitrile; 2.1: Luche reduction / 9.1: Tamao oxidation;

DOI:10.1002/asia.200800429

Reference yield:

C52H66O7Si2 (1018988-59-4) → C17H20(OH)2(OCOCH3)2(CH2OCOCH3)(CH3)(OCOC6H4OCH3)(CHCH2) (1018988-55-0)

Guidance literature:

Multi-step reaction with 17 steps

1.1: sodium tetrahydroborate / ethanol / 2 h / -78 °C / Inert atmosphere

2.1: dichloromethane / 1 h / 20 °C / Inert atmosphere; Molecular sieve

2.2: 39 h / 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: 2,6-di-tert-butyl-4-methylpyridine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetonitrile / 20 °C / Inert atmosphere

5.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / -40 - -30 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 13 °C / Inert atmosphere

7.1: lithium borohydride / tetrahydrofuran / Inert atmosphere; Reflux

7.2: 4 h / 20 °C / Inert atmosphere

8.1: lithium borohydride / tetrahydrofuran / 26.5 h / 20 °C / Inert atmosphere; Reflux

8.2: 4 h / 20 °C / Inert atmosphere

9.1: water; acetic acid / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

10.1: dmap / pyridine; dichloromethane / 24 h / 20 °C / Inert atmosphere

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

12.1: peracetic acid; mercury(II) diacetate; acetic acid / 4 h / 20 °C / Inert atmosphere

13.1: 1H-imidazole / dichloromethane / 4 h / 0 °C / Inert atmosphere

14.1: dmap / pyridine; dichloromethane / 0 - 40 °C / Inert atmosphere

15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

16.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

17.1: Wilkinson's catalyst; triphenylphosphine; isopropyl alcohol / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

With 1H-imidazole; peracetic acid; dmap; sodium tetrahydroborate; Wilkinson's catalyst; lithium borohydride; 2,6-di-tert-butyl-4-methylpyridine; mercury(II) diacetate; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; isopropyl alcohol; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; ethanol; dichloromethane; acetonitrile; 5.1: Luche reduction / 12.1: Tamao oxidation;

DOI:10.1002/asia.200800429

upstream raw materials:

C₃₄H₄₄O₁₂

diazomethyl-trimethyl-silane

C₅₂H₆₆O₇Si₂

C₅₂H₆₈O₇Si₂

Downstream raw materials:

C₃₅H₄₈O₁₃

C₃₇H₄₆O₁₃

C₃₅H₄₆O₁₃

C₅₅H₆₂O₁₆

Refernces

• 1、 Zhang, Hongxing,Sridhar Reddy, Maddi,Phoenix, Serge,Deslongchamps, Pierre. "Total synthesis of ouabagenin and ouabain". . p. 1272 - 1275. Retrieved 2008/12/22.