[2-((2S,3S,8R,9S)-8-benzyloxy-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-ethoxy]-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: [2-((2S,3S,8R,9S)-8-benzyloxy-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-ethoxy]-tert-butyl-diphenyl-silane
• CAS No.: 558459-44-2
• Molecular Formula: C₃₅H₄₅ClO₃Si
• Molecular Weight: 577.279

Synonyms:[2-((2S,3S,8R,9S)-8-benzyloxy-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-ethoxy]-tert-butyl-diphenyl-silane

Chemical Property of [2-((2S,3S,8R,9S)-8-benzyloxy-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-ethoxy]-tert-butyl-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of [2-((2S,3S,8R,9S)-8-benzyloxy-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-ethoxy]-tert-butyl-diphenyl-silane

There total 17 articles about [2-((2S,3S,8R,9S)-8-benzyloxy-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-ethoxy]-tert-butyl-diphenyl-silane 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: 64.0%

(2S,3R,8R,9S)-8-benzyloxy-2-[2-(tert-butyl-diphenyl-silanyloxy)ethyl]-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-3-ol (558459-43-1) → [2-((3Z,5Z)-(2S,8R,9S)-8-Benzyloxy-9-ethyl-2,7,8,9-tetrahydro-oxonin-2-yl)-ethoxy]-tert-butyl-diphenyl-silane + [2-((2S,3S,8R,9S)-8-benzyloxy-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-ethoxy]-tert-butyl-diphenyl-silane (558459-44-2)

Guidance literature:

With tetrachloromethane; 1-methylcyclohex-1-ene; TOP; In toluene; at 80 ℃;

DOI:10.1021/ja029956v

Reference yield:

(2S)-2-[(1R)-1-benzyloxy-but-3-enyl]-oxirane (99838-72-9) → [2-((2S,3S,8R,9S)-8-benzyloxy-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-ethoxy]-tert-butyl-diphenyl-silane (558459-44-2)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 90 percent / CuI / tetrahydrofuran; diethyl ether / 1 h / -20 °C

2.1: NaH / tetrahydrofuran / 0 - 25 °C

2.2: 90 percent / tetrahydrofuran / 10 h / 25 °C

3.1: Et₃N / diethyl ether / -78 - 0 °C

4.1: n-BuLi / tetrahydrofuran; hexane

4.2: 28.6 g / tetrahydrofuran; hexane / -78 - 0 °C

5.1: NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -78 °C

5.2: 82 percent / tetrahydrofuran / 1.5 h / -40 °C

6.1: 82 percent / NaBH₄ / tetrahydrofuran; H₂O / 14 h / 25 °C

7.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -15 °C

8.1: methoxyborane derived from 2-carene / diethyl ether / 1 h

8.2: diethyl ether / 2 h

8.3: aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 3 h / Heating

9.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h

10.1: 80 percent / meta-chloroperoxybenzoic acid / CH₂Cl₂ / -40 - 25 °C

11.1: 80 percent / (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / 14 h

12.1: 65 percent / aq. HClO₄ / tetrahydrofuran / 8 h

13.1: aq. NaIO₄; Bu₄NHSO₄ / tetrahydrofuran / 2 h

14.1: 65 percent / NaBH₄ / methanol / 0.5 h

15.1: 90 percent / TBAF / tetrahydrofuran / 2 h

16.1: 91 percent / imidazole / dimethylformamide / 14 h

17.1: 64 percent / trioctylphosphine; 1-methyl-1-cyclohexene; CCl₄ / toluene / 80 °C

With 1H-imidazole; 2,6-dimethylpyridine; tetrachloromethane; sodium tetrahydroborate; sodium periodate; copper(l) iodide; Grubbs catalyst first generation; n-butyllithium; perchloric acid; 1-methylcyclohex-1-ene; oxalyl dichloride; TOP; methoxyborane derived from 2-carene; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; sodium hexamethyldisilazane; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 7.1: Swern oxidation;

DOI:10.1021/ja029956v

Reference yield:

(3S,4R)-4-benzyloxy-hept-6-en-3-ol (558459-28-2) → [2-((2S,3S,8R,9S)-8-benzyloxy-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-ethoxy]-tert-butyl-diphenyl-silane (558459-44-2)

Guidance literature:

Multi-step reaction with 16 steps

1.1: NaH / tetrahydrofuran / 0 - 25 °C

1.2: 90 percent / tetrahydrofuran / 10 h / 25 °C

2.1: Et₃N / diethyl ether / -78 - 0 °C

3.1: n-BuLi / tetrahydrofuran; hexane

3.2: 28.6 g / tetrahydrofuran; hexane / -78 - 0 °C

4.1: NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -78 °C

4.2: 82 percent / tetrahydrofuran / 1.5 h / -40 °C

5.1: 82 percent / NaBH₄ / tetrahydrofuran; H₂O / 14 h / 25 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -15 °C

7.1: methoxyborane derived from 2-carene / diethyl ether / 1 h

7.2: diethyl ether / 2 h

7.3: aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 3 h / Heating

8.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h

9.1: 80 percent / meta-chloroperoxybenzoic acid / CH₂Cl₂ / -40 - 25 °C

10.1: 80 percent / (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / 14 h

11.1: 65 percent / aq. HClO₄ / tetrahydrofuran / 8 h

12.1: aq. NaIO₄; Bu₄NHSO₄ / tetrahydrofuran / 2 h

13.1: 65 percent / NaBH₄ / methanol / 0.5 h

14.1: 90 percent / TBAF / tetrahydrofuran / 2 h

15.1: 91 percent / imidazole / dimethylformamide / 14 h

16.1: 64 percent / trioctylphosphine; 1-methyl-1-cyclohexene; CCl₄ / toluene / 80 °C

With 1H-imidazole; 2,6-dimethylpyridine; tetrachloromethane; sodium tetrahydroborate; sodium periodate; Grubbs catalyst first generation; n-butyllithium; perchloric acid; 1-methylcyclohex-1-ene; oxalyl dichloride; TOP; methoxyborane derived from 2-carene; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; sodium hexamethyldisilazane; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 6.1: Swern oxidation;

DOI:10.1021/ja029956v

upstream raw materials:

(2S,3R,8R,9S)-8-benzyloxy-2-[2-(tert-butyl-diphenyl-silanyloxy)ethyl]-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-3-ol

(2S)-2-[(1R)-1-benzyloxy-but-3-enyl]-oxirane

(3S,4R)-4-benzyloxy-hept-6-en-3-ol

[(1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy]-acetic acid

Downstream raw materials:

[(2S,3S,8S,9S)-2-(8-bromo-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-ethoxy]-tert-butyl-diphenyl-silane

(+)-obtusenyne

(2S,3R,8S,9S)-9-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-8-chloro-2-ethyl-2,3,4,7,8,9-hexahydro-oxonin-3-ol

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