(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

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)-1-hydroxyethyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one
• CAS No.: 1352577-42-4
• Molecular Formula: C₃₇H₅₇NO₅Si
• Molecular Weight: 623.949
• Mol file: 1352577-42-4.mol

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)-1-hydroxyethyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one

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)-1-hydroxyethyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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)-1-hydroxyethyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one

There total 17 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)-1-hydroxyethyl)-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: 90.0%

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)ethanal (1352577-41-3) + (5R)-1-benzoyl-5-(2-methylpropyl)pyrrolidin-2-one (124575-36-6) → (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 (1352577-42-4)

Guidance literature:

(5R)-1-benzoyl-5-(2-methylpropyl)pyrrolidin-2-one; With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h; Inert atmosphere;

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)ethanal; In tetrahydrofuran; hexane; at -78 ℃; for 4h; Inert atmosphere;

With acetic acid; In tetrahydrofuran; hexane; at -78 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.079

Reference yield:

(1S,2S,7S,8S,9R)-9-(tert-butyldimethylsilyloxy)-1-methyl-4,12-dioxa-tricyclo[6.3.1.0(2,7)]dodecan-3-one (1352577-36-6) → (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 (1352577-42-4)

Guidance literature:

Multi-step reaction with 9 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

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;

DOI:10.1016/j.tet.2011.09.079

Reference yield:

(1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-hydroxyethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carboxylic acid (1352577-48-0) → (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 (1352577-42-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16.25 h / 23 - 35 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 20 h / 75 °C / Inert atmosphere

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

3.2: 1.5 h / -40 - 23 °C / Inert atmosphere

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

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

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

7.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide / tetrahydrofuran; water / 0.5 h / 23 °C / Inert atmosphere

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

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

9.2: 0.5 h / -78 - 23 °C / Inert atmosphere

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

10.2: 4 h / -78 °C / Inert atmosphere

10.3: -78 °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; benzotriazol-1-ol; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; benzene; 7.1: Suzuki coupling / 9.1: Swern oxidation / 9.2: Swern oxidation;

DOI:10.1016/j.tet.2011.09.079

upstream raw materials:

(1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-hydroxyethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carboxylic acid

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

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

2-((1S,4R,5S,6S,7S)-4-(tert-butyldimethylsilyloxy)-7-(hydroxymethyl)-1-methyl-8-oxabicyclo[3.2.1]octan-6-yl)ethanol

Downstream raw materials:

(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

(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)-3-(phenylselanyl)pyrrolidin-2-one

N-benzoyl-O-tert-butyldimethylsilyl-aspergillin PZ