(5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanoyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one

Base Information

Chemical Name:(5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanoyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one
CAS No.:1352577-43-5
Molecular Formula:C₃₇H₅₅NO₅Si
Molecular Weight:621.933
Hs Code.:

(5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanoyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one

Synonyms:(5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanoyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one

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Chemical Property of (5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanoyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one

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Technology Process of (5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanoyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one

There total 20 articles about (5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanoyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-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: 42.0%

: 1352577-42-4
(5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)-1-hydroxyethyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one

: 1352577-43-5
(5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanoyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one

Guidance literature:: (5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)-1-hydroxyethyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 2h; Inert atmosphere;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 23 ℃; for 0.25h; Inert atmosphere;
DOI:10.1016/j.tet.2011.09.079

Reference yield:

: 1352577-37-7
(1S,2R,7S,8S,9R)-9-(tert-butyldimethylsilyloxy)-1-methyl-4,12-dioxa-tricyclo[6.3.1.0(2,7)]dodecan-3-one

: 1352577-43-5
(5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanoyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 42 h / -40 °C / Inert atmosphere

1.2: 1.5 h / -40 - 23 °C / Inert atmosphere

2.1: pyridine; dmap / 21 h / 23 °C / Inert atmosphere

3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1.12 h / 0 - 23 °C / Inert atmosphere; Molecular sieve

4.1: chromium dichloride / tetrahydrofuran / 5.08 h / 0 - 23 °C / Inert atmosphere

5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide / tetrahydrofuran; water / 0.5 h / 23 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 44 h / 23 °C / Inert atmosphere

7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

7.2: 0.5 h / -78 - 23 °C / Inert atmosphere

8.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere

8.2: 4 h / -78 °C / Inert atmosphere

8.3: -78 °C / Inert atmosphere

9.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C / Inert atmosphere

9.2: 0.25 h / -78 - 23 °C / Inert atmosphere

With pyridine; chromium dichloride; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; oxalyl dichloride; tetrabutyl ammonium fluoride; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; potassium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; 5.1: Suzuki coupling / 7.1: Swern oxidation / 7.2: Swern oxidation / 9.1: Swern oxidation / 9.2: Swern oxidation;
DOI:10.1016/j.tet.2011.09.079

Reference yield:

: 1352577-36-6
(1S,2S,7S,8S,9R)-9-(tert-butyldimethylsilyloxy)-1-methyl-4,12-dioxa-tricyclo[6.3.1.0(2,7)]dodecan-3-one

: 1352577-43-5
(5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanoyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 20 h / 75 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / diethyl ether / 42 h / -40 °C / Inert atmosphere

2.2: 1.5 h / -40 - 23 °C / Inert atmosphere

3.1: pyridine; dmap / 21 h / 23 °C / Inert atmosphere

4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1.12 h / 0 - 23 °C / Inert atmosphere; Molecular sieve

5.1: chromium dichloride / tetrahydrofuran / 5.08 h / 0 - 23 °C / Inert atmosphere

6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide / tetrahydrofuran; water / 0.5 h / 23 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 44 h / 23 °C / Inert atmosphere

8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

8.2: 0.5 h / -78 - 23 °C / Inert atmosphere

9.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere

9.2: 4 h / -78 °C / Inert atmosphere

9.3: -78 °C / Inert atmosphere

10.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C / Inert atmosphere

10.2: 0.25 h / -78 - 23 °C / Inert atmosphere

With pyridine; chromium dichloride; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; oxalyl dichloride; tetrabutyl ammonium fluoride; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; benzene; 6.1: Suzuki coupling / 8.1: Swern oxidation / 8.2: Swern oxidation / 10.1: Swern oxidation / 10.2: Swern oxidation;
DOI:10.1016/j.tet.2011.09.079