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

Base Information

• Chemical Name: 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
• CAS No.: 911236-88-9
• Molecular Formula: C₆₄H₁₀₀O₁₀Si₂
• Molecular Weight: 1085.66
• Mol file: 911236-88-9.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 47 articles about 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 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: 66.0%

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 (911236-87-8) → 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 (911236-88-9)

Guidance literature:

With potassium carbonate; In methanol; at 65 ℃;

DOI:10.1021/ol0615782

Reference yield:

(S)-4-(4-Methoxy-benzyloxy)-6-methyl-hept-6-ene-1,3-diol (911236-94-7) → 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 (911236-88-9)

Guidance literature:

Multi-step reaction with 21 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

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; 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) → 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 (911236-88-9)

Guidance literature:

Multi-step reaction with 18 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

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; 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

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

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

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

(S)-4-(4-Methoxy-benzyloxy)-6-methyl-hept-6-ene-1,3-diol

Downstream raw materials:

C₄₂H₆₀O₉

C₅₀H₆₈O₁₀

C₄₁H₅₈O₈