C₄₂H₆₀O₉

Base Information

• Chemical Name: C₄₂H₆₀O₉
• CAS No.: 911236-90-3
• Molecular Formula: C₄₂H₆₀O₉
• Molecular Weight: 708.933

Synonyms:C₄₂H₆₀O₉

Chemical Property of C₄₂H₆₀O₉

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₄₂H₆₀O₉

There total 49 articles about C₄₂H₆₀O₉ 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:

(S)-4-(4-Methoxy-benzyloxy)-6-methyl-hept-6-ene-1,3-diol (911236-94-7) → C42H60O9 (911236-90-3)

Guidance literature:

Multi-step reaction with 22 steps

1.1: 100 percent / imidazole / CH₂Cl₂

2.1: 100 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 °C

3.1: 79 percent / Zn(BH₄)2 / diethyl ether / -40 - -25 °C

4.1: NaH / dimethylformamide; tetrahydrofuran / 0.17 h / 0 °C

4.2: 90 percent / dimethylformamide; tetrahydrofuran / 0 - 20 °C

5.1: Et₃N / tetrahydrofuran / -78 - 0 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 27.6 g / tetrahydrofuran; hexane / 1.75 h / -78 - 0 °C

7.1: NaN(SiMe₃)2 / tetrahydrofuran; toluene / 1 h / -78 °C

7.2: 83 percent / tetrahydrofuran; toluene / 1 h / -78 °C

8.1: 86 percent / LiBH₄ / methanol; diethyl ether / 1 h / 0 °C

9.1: 99 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 °C

10.1: Mg; I₂ / tetrahydrofuran / 0.5 h

10.2: 86 percent / tetrahydrofuran / 0.08 h / 0 °C

11.1: 52 percent / Cl₂(PCy₃)(Imes)Ru=CHPh / CH₂Cl₂ / Heating

12.1: 94 percent / [PCy₃][COD][Pyr]Ir⁽¹⁺⁾*PF₆^(1-); H₂ / CH₂Cl₂ / -50 °C

13.1: 95 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 °C

14.1: 88 percent / tetrahydrofuran; diethyl ether / 0.33 h / -78 °C

15.1: 95 percent / H₂ / Raney nickel / ethanol; H₂O

16.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

17.1: Ba(OH)2 / tetrahydrofuran / 0.5 h / 20 °C

17.2: 96 percent / tetrahydrofuran; H₂O / 0.5 h / 20 °C

18.1: 92 percent / Me₂PhSiH; (PPh₃)3RhCl / toluene / 50 °C

19.1: dimethyldioxirane / CH₂Cl₂ / -78 °C

19.2: i-Bu₂AlH / CH₂Cl₂; hexane / -78 °C

20.1: 0.080 g / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

21.1: 66 percent / K₂CO₃ / methanol / 65 °C

22.1: 34 percent / camphorsulfonic acid / 3 h / Heating

With 1H-imidazole; barium dihydroxide; Wilkinson's catalyst; lithium borohydride; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; n-butyllithium; zinc(II) tetrahydroborate; oxalyl dichloride; (η4-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate; Dimethylphenylsilane; camphor-10-sulfonic acid; hydrogen; iodine; sodium hexamethyldisilazane; 3,3-dimethyldioxirane; sodium hydride; potassium carbonate; Dess-Martin periodane; magnesium; dimethyl sulfoxide; triethylamine; nickel; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2.1: Swern oxidation / 9.1: Swern oxidation / 13.1: Swern oxidation;

DOI:10.1021/ol0615782

Reference yield:

(3R,4S)-4-(4-Methoxy-benzyloxy)-6-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol (911236-72-1) → C42H60O9 (911236-90-3)

Guidance literature:

Multi-step reaction with 19 steps

1.1: NaH / dimethylformamide; tetrahydrofuran / 0.17 h / 0 °C

1.2: 90 percent / dimethylformamide; tetrahydrofuran / 0 - 20 °C

2.1: Et₃N / tetrahydrofuran / -78 - 0 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 27.6 g / tetrahydrofuran; hexane / 1.75 h / -78 - 0 °C

4.1: NaN(SiMe₃)2 / tetrahydrofuran; toluene / 1 h / -78 °C

4.2: 83 percent / tetrahydrofuran; toluene / 1 h / -78 °C

5.1: 86 percent / LiBH₄ / methanol; diethyl ether / 1 h / 0 °C

6.1: 99 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 °C

7.1: Mg; I₂ / tetrahydrofuran / 0.5 h

7.2: 86 percent / tetrahydrofuran / 0.08 h / 0 °C

8.1: 52 percent / Cl₂(PCy₃)(Imes)Ru=CHPh / CH₂Cl₂ / Heating

9.1: 94 percent / [PCy₃][COD][Pyr]Ir⁽¹⁺⁾*PF₆^(1-); H₂ / CH₂Cl₂ / -50 °C

10.1: 95 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 °C

11.1: 88 percent / tetrahydrofuran; diethyl ether / 0.33 h / -78 °C

12.1: 95 percent / H₂ / Raney nickel / ethanol; H₂O

13.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

14.1: Ba(OH)2 / tetrahydrofuran / 0.5 h / 20 °C

14.2: 96 percent / tetrahydrofuran; H₂O / 0.5 h / 20 °C

15.1: 92 percent / Me₂PhSiH; (PPh₃)3RhCl / toluene / 50 °C

16.1: dimethyldioxirane / CH₂Cl₂ / -78 °C

16.2: i-Bu₂AlH / CH₂Cl₂; hexane / -78 °C

17.1: 0.080 g / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

18.1: 66 percent / K₂CO₃ / methanol / 65 °C

19.1: 34 percent / camphorsulfonic acid / 3 h / Heating

With barium dihydroxide; Wilkinson's catalyst; lithium borohydride; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; n-butyllithium; oxalyl dichloride; (η4-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate; Dimethylphenylsilane; camphor-10-sulfonic acid; hydrogen; iodine; sodium hexamethyldisilazane; 3,3-dimethyldioxirane; sodium hydride; potassium carbonate; Dess-Martin periodane; magnesium; dimethyl sulfoxide; triethylamine; nickel; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 6.1: Swern oxidation / 10.1: Swern oxidation;

DOI:10.1021/ol0615782

Reference yield:

(S)-4-(4-Methoxy-benzyloxy)-6-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol (911236-95-8) → C42H60O9 (911236-90-3)

Guidance literature:

Multi-step reaction with 21 steps

1.1: 100 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 79 percent / Zn(BH₄)2 / diethyl ether / -40 - -25 °C

3.1: NaH / dimethylformamide; tetrahydrofuran / 0.17 h / 0 °C

3.2: 90 percent / dimethylformamide; tetrahydrofuran / 0 - 20 °C

4.1: Et₃N / tetrahydrofuran / -78 - 0 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: 27.6 g / tetrahydrofuran; hexane / 1.75 h / -78 - 0 °C

6.1: NaN(SiMe₃)2 / tetrahydrofuran; toluene / 1 h / -78 °C

6.2: 83 percent / tetrahydrofuran; toluene / 1 h / -78 °C

7.1: 86 percent / LiBH₄ / methanol; diethyl ether / 1 h / 0 °C

8.1: 99 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 °C

9.1: Mg; I₂ / tetrahydrofuran / 0.5 h

9.2: 86 percent / tetrahydrofuran / 0.08 h / 0 °C

10.1: 52 percent / Cl₂(PCy₃)(Imes)Ru=CHPh / CH₂Cl₂ / Heating

11.1: 94 percent / [PCy₃][COD][Pyr]Ir⁽¹⁺⁾*PF₆^(1-); H₂ / CH₂Cl₂ / -50 °C

12.1: 95 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 °C

13.1: 88 percent / tetrahydrofuran; diethyl ether / 0.33 h / -78 °C

14.1: 95 percent / H₂ / Raney nickel / ethanol; H₂O

15.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

16.1: Ba(OH)2 / tetrahydrofuran / 0.5 h / 20 °C

16.2: 96 percent / tetrahydrofuran; H₂O / 0.5 h / 20 °C

17.1: 92 percent / Me₂PhSiH; (PPh₃)3RhCl / toluene / 50 °C

18.1: dimethyldioxirane / CH₂Cl₂ / -78 °C

18.2: i-Bu₂AlH / CH₂Cl₂; hexane / -78 °C

19.1: 0.080 g / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

20.1: 66 percent / K₂CO₃ / methanol / 65 °C

21.1: 34 percent / camphorsulfonic acid / 3 h / Heating

With barium dihydroxide; Wilkinson's catalyst; lithium borohydride; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; n-butyllithium; zinc(II) tetrahydroborate; oxalyl dichloride; (η4-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate; Dimethylphenylsilane; camphor-10-sulfonic acid; hydrogen; iodine; sodium hexamethyldisilazane; 3,3-dimethyldioxirane; sodium hydride; potassium carbonate; Dess-Martin periodane; magnesium; dimethyl sulfoxide; triethylamine; nickel; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Swern oxidation / 8.1: Swern oxidation / 12.1: Swern oxidation;

DOI:10.1021/ol0615782

upstream raw materials:

2-{2-[8-benzyloxy-9-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-propyl}-7-(4-methoxy-benzyloxy)-9,10a-dimethyl-6-(2-triisopropylsilanyloxy-ethyl)-octahydro-1,5-dioxa-benzocycloocten-3-one

methanol

(S)-2-(4-methoxybenzyloxy)pent-4-enal

(2S)-2-(4-methoxybenzyloxy)-4-pentenol

Downstream raw materials:

C₄₁H₅₈O₈

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