3-{(2S,5S)-5-[(3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-5-methylhexyl]-4-methylenetetrahydrofuran-2-yl}propyl pivalate

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Chemical Name:3-{(2S,5S)-5-[(3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-5-methylhexyl]-4-methylenetetrahydrofuran-2-yl}propyl pivalate
CAS No.:1417995-91-5
Molecular Formula:C₃₈H₅₈O₆Si
Molecular Weight:638.96
Hs Code.:

Synonyms:3-{(2S,5S)-5-[(3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-5-methylhexyl]-4-methylenetetrahydrofuran-2-yl}propyl pivalate

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Chemical Property of 3-{(2S,5S)-5-[(3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-5-methylhexyl]-4-methylenetetrahydrofuran-2-yl}propyl pivalate

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Technology Process of 3-{(2S,5S)-5-[(3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-5-methylhexyl]-4-methylenetetrahydrofuran-2-yl}propyl pivalate

There total 21 articles about 3-{(2S,5S)-5-[(3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-5-methylhexyl]-4-methylenetetrahydrofuran-2-yl}propyl pivalate 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: 85.0%

: 1417996-08-7
3-{(2S,5S)-5-[(3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-5-methylhexyl]-4-oxotetrahydrofuran-2-yl}propyl pivalate

: 1779-49-3
Methyltriphenylphosphonium bromide

: 1417995-91-5
3-{(2S,5S)-5-[(3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-5-methylhexyl]-4-methylenetetrahydrofuran-2-yl}propyl pivalate

Guidance literature:: Methyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

3-{(2S,5S)-5-[(3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-5-methylhexyl]-4-oxotetrahydrofuran-2-yl}propyl pivalate; In tetrahydrofuran; at 0 - 20 ℃; for 1.25h;
DOI:10.1002/ejoc.201201119

Reference yield:

: 1417995-97-1
(R)-4-benzyl-3-[(S)-4-(methoxymethoxy)hept-6-enoyl]oxazolidin-2-one

: 1417995-91-5
3-{(2S,5S)-5-[(3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-5-methylhexyl]-4-methylenetetrahydrofuran-2-yl}propyl pivalate

Guidance literature:: Multi-step reaction with 11 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 3.5 h / -75 °C / Inert atmosphere

2.1: sodium tetrahydroborate / tetrahydrofuran; water / 1 h / 0 - 20 °C / Inert atmosphere

3.1: 1H-imidazole / dichloromethane / 0.5 h / -20 °C / Inert atmosphere

4.1: dimethylsulfide borane complex / tetrahydrofuran / 0 °C / Inert atmosphere

4.2: 2 h / Inert atmosphere

5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

6.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / -78 °C / Inert atmosphere

6.2: Julia-Kocienski Olefination / -78 °C / Inert atmosphere

7.1: pyridinium p-toluenesulfonate / ethanol / 6 h / 55 °C / Inert atmosphere

8.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

9.1: potassium osmate(VI) dihydrate; methanesulfonamide; AD-mix alpha / water; tert-butyl alcohol / 0 - 20 °C / Inert atmosphere

10.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

11.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

11.2: 1.25 h / 0 - 20 °C

With 1H-imidazole; potassium osmate(VI) dihydrate; sodium tetrahydroborate; methanesulfonamide; dimethylsulfide borane complex; AD-mix alpha; potassium tert-butylate; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; Dess-Martin periodane; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; tert-butyl alcohol; 6.1: |Julia-Kocienski Olefination / 11.1: |Wittig Olefination;
DOI:10.1002/ejoc.201201119

Reference yield:

: 127793-67-3
(S)‐7‐(benzyloxy)hept‐1‐en‐4‐ol

: 1417995-91-5
3-{(2S,5S)-5-[(3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-5-methylhexyl]-4-methylenetetrahydrofuran-2-yl}propyl pivalate

Guidance literature:: Multi-step reaction with 15 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

2.1: naphthalene; lithium / tetrahydrofuran / 0.42 h / -20 °C / Inert atmosphere

3.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-tetramethyl-piperidine-N-oxyl / dichloromethane; water / 4 h / 0 - 20 °C / Inert atmosphere

4.1: triethylamine; pivaloyl chloride / tetrahydrofuran / -20 °C / Inert atmosphere

4.2: 0.5 h / -20 °C / Inert atmosphere

4.3: -20 - 20 °C / Inert atmosphere

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

5.2: 3.5 h / -75 °C / Inert atmosphere

6.1: sodium tetrahydroborate / tetrahydrofuran; water / 1 h / 0 - 20 °C / Inert atmosphere

7.1: 1H-imidazole / dichloromethane / 0.5 h / -20 °C / Inert atmosphere

8.1: dimethylsulfide borane complex / tetrahydrofuran / 0 °C / Inert atmosphere

8.2: 2 h / Inert atmosphere

9.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

10.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / -78 °C / Inert atmosphere

10.2: Julia-Kocienski Olefination / -78 °C / Inert atmosphere

11.1: pyridinium p-toluenesulfonate / ethanol / 6 h / 55 °C / Inert atmosphere

12.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

13.1: potassium osmate(VI) dihydrate; methanesulfonamide; AD-mix alpha / water; tert-butyl alcohol / 0 - 20 °C / Inert atmosphere

14.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

15.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

15.2: 1.25 h / 0 - 20 °C

With 1H-imidazole; potassium osmate(VI) dihydrate; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; naphthalene; methanesulfonamide; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; AD-mix alpha; potassium tert-butylate; pyridinium p-toluenesulfonate; pivaloyl chloride; lithium; potassium hexamethylsilazane; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; tert-butyl alcohol; 10.1: |Julia-Kocienski Olefination / 15.1: |Wittig Olefination;
DOI:10.1002/ejoc.201201119