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

Base Information

• Chemical Name: N-benzoyl-O-tert-butyldimethylsilyl-aspergillin PZ
• CAS No.: 1352577-45-7
• Molecular Formula: C₃₇H₅₃NO₅Si
• Molecular Weight: 619.917
• Mol file: 1352577-45-7.mol

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

Chemical Property of N-benzoyl-O-tert-butyldimethylsilyl-aspergillin PZ

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzoyl-O-tert-butyldimethylsilyl-aspergillin PZ

There total 23 articles about N-benzoyl-O-tert-butyldimethylsilyl-aspergillin PZ 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:

(S)-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)-1H-pyrrol-2(5H)-one → N-benzoyl-O-tert-butyldimethylsilyl-aspergillin PZ (1352577-45-7)

Guidance literature:

In chloroform-d1; toluene; at 100 ℃; for 5.5h; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.079

Reference yield:

2-((1S,4R,5S,6S,7S)-4-(tert-butyldimethylsilyloxy)-7-(hydroxymethyl)-1-methyl-8-oxabicyclo[3.2.1]octan-6-yl)ethanol (1352577-49-1) → N-benzoyl-O-tert-butyldimethylsilyl-aspergillin PZ (1352577-45-7)

Guidance literature:

Multi-step reaction with 11 steps

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

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

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

4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide / tetrahydrofuran; water / 0.5 h / 23 °C / Inert atmosphere

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

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

6.2: 0.5 h / -78 - 23 °C / Inert atmosphere

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

7.2: 4 h / -78 °C / Inert atmosphere

7.3: -78 °C / Inert atmosphere

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

8.2: 0.25 h / -78 - 23 °C / Inert atmosphere

9.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

9.2: 2 h / -78 °C / Inert atmosphere

10.1: dihydrogen peroxide; 3-chloro-benzenecarboperoxoic acid / chloroform-d1; water / 1.17 h / -50 - 0 °C / Inert atmosphere

11.1: chloroform-d1; toluene / 5.5 h / 100 °C / Inert atmosphere

With pyridine; chromium dichloride; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrapropylammonium perruthennate; oxalyl dichloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; potassium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; chloroform-d1; hexane; dichloromethane; water; toluene; 4.1: Suzuki coupling / 6.1: Swern oxidation / 6.2: Swern oxidation / 8.1: Swern oxidation / 8.2: Swern oxidation / 11.1: Diels-Alder reaction;

DOI:10.1016/j.tet.2011.09.079

Reference yield:

((1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octan-6-yl)methanol (1352577-38-8) → N-benzoyl-O-tert-butyldimethylsilyl-aspergillin PZ (1352577-45-7)

Guidance literature:

Multi-step reaction with 10 steps

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

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

3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide / tetrahydrofuran; water / 0.5 h / 23 °C / Inert atmosphere

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

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

5.2: 0.5 h / -78 - 23 °C / Inert atmosphere

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

6.2: 4 h / -78 °C / Inert atmosphere

6.3: -78 °C / Inert atmosphere

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

7.2: 0.25 h / -78 - 23 °C / Inert atmosphere

8.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

8.2: 2 h / -78 °C / Inert atmosphere

9.1: dihydrogen peroxide; 3-chloro-benzenecarboperoxoic acid / chloroform-d1; water / 1.17 h / -50 - 0 °C / Inert atmosphere

10.1: chloroform-d1; toluene / 5.5 h / 100 °C / Inert atmosphere

With chromium dichloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrapropylammonium perruthennate; oxalyl dichloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; potassium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; chloroform-d1; hexane; dichloromethane; water; toluene; 3.1: Suzuki coupling / 5.1: Swern oxidation / 5.2: Swern oxidation / 7.1: Swern oxidation / 7.2: Swern oxidation / 10.1: Diels-Alder reaction;

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