3-((1R,4S,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2,5-dimethylcyclopent-2-en-1-yl)-4-hydroxy-5-phenylpyridin-2(1H)-one

Base Information

• Chemical Name: 3-((1R,4S,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2,5-dimethylcyclopent-2-en-1-yl)-4-hydroxy-5-phenylpyridin-2(1H)-one
• CAS No.: 1268265-17-3
• Molecular Formula: C₃₅H₃₉NO₃Si
• Molecular Weight: 549.785
• Mol file: 1268265-17-3.mol

Synonyms:3-((1R,4S,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2,5-dimethylcyclopent-2-en-1-yl)-4-hydroxy-5-phenylpyridin-2(1H)-one

Chemical Property of 3-((1R,4S,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2,5-dimethylcyclopent-2-en-1-yl)-4-hydroxy-5-phenylpyridin-2(1H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((1R,4S,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2,5-dimethylcyclopent-2-en-1-yl)-4-hydroxy-5-phenylpyridin-2(1H)-one

There total 13 articles about 3-((1R,4S,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2,5-dimethylcyclopent-2-en-1-yl)-4-hydroxy-5-phenylpyridin-2(1H)-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: 66.0%

ethyl 2-((1S,4S,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2,5-dimethylcyclopent-2-en-1-yl)-3-oxo-3-((E)-styrylamino)propanoate (1268265-23-1) → 3-((1R,4S,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2,5-dimethylcyclopent-2-en-1-yl)-4-hydroxy-5-phenylpyridin-2(1H)-one (1268265-17-3)

Guidance literature:

In diphenylether; at 210 ℃; for 0.75h; Inert atmosphere;

DOI:10.1021/ol200022a

Reference yield:

(2R,3R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methylcyclopentanone (876152-36-2) → 3-((1R,4S,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2,5-dimethylcyclopent-2-en-1-yl)-4-hydroxy-5-phenylpyridin-2(1H)-one (1268265-17-3)

Guidance literature:

Multi-step reaction with 7 steps

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

1.2: 0.67 h / -78 °C / Inert atmosphere

1.3: 19 h / 20 °C / Inert atmosphere

2.1: pyridine; iodine / tetrachloromethane / 11.5 h / 20 °C / Inert atmosphere

3.1: copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; triphenyl-arsane / 1-methyl-pyrrolidin-2-one / 6 h / 80 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -78 °C / Inert atmosphere

5.1: N,N,N,N,-tetramethylethylenediamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

6.1: 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)); sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

7.1: diphenylether / 0.75 h / 210 °C / Inert atmosphere

With pyridine; 1,1'-bis-(diphenylphosphino)ferrocene; copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; bis(η3-allyl-μ-chloropalladium(II)); N,N,N,N,-tetramethylethylenediamine; triphenyl-arsane; iodine; sodium hydride; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; tetrachloromethane; diphenylether; hexane; dichloromethane; 3.1: Stille coupling;

DOI:10.1021/ol200022a

Reference yield:

(4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-methylcyclopent-2-enone (1268265-20-8) → 3-((1R,4S,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2,5-dimethylcyclopent-2-en-1-yl)-4-hydroxy-5-phenylpyridin-2(1H)-one (1268265-17-3)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine; iodine / tetrachloromethane / 11.5 h / 20 °C / Inert atmosphere

2: copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; triphenyl-arsane / 1-methyl-pyrrolidin-2-one / 6 h / 80 °C / Inert atmosphere

3: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -78 °C / Inert atmosphere

4: N,N,N,N,-tetramethylethylenediamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

5: 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)); sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

6: diphenylether / 0.75 h / 210 °C / Inert atmosphere

With pyridine; 1,1'-bis-(diphenylphosphino)ferrocene; copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; bis(η3-allyl-μ-chloropalladium(II)); N,N,N,N,-tetramethylethylenediamine; triphenyl-arsane; iodine; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; tetrachloromethane; diphenylether; hexane; dichloromethane; 2: Stille coupling;

DOI:10.1021/ol200022a

upstream raw materials:

(2R,3R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methylcyclopentanone

tert-butyl(((1S,2R)-2-methyl-5-(propan-2-ylidene)cyclopentyl)methoxy)diphenylsilane

(4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-methylcyclopent-2-enone

(4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-4-methylcyclopent-2-enone

Downstream raw materials:

(5aR,6R,7R,8R,8aS)-7-(((tert-butyldiphenylsilyl)oxy)methyl)-6-iodo-5a,8-dimethyl-4-phenyl-2,5a,6,7,8,8a-hexahydro-1H-cyclopenta[4,5]furo[3,2-c]pyridin-1-one

(5aR,6R,7R,8R,8aS)-7-(hydroxymethyl)-6-iodo-5a,8-dimethyl-4-phenyl-2,5a,6,7,8,8a-hexahydro-1H-cyclopenta[4,5]furo[3,2-c]pyridin-1-one

(5aS,8R,8aS)-5a,8-dimethyl-1-oxo-4-phenyl-2,5a,8,8a-tetrahydro-1H-cyclopenta[4,5]furo[3,2-c]pyridine-7-carbaldehyde

(5aS,8R,8aS)-7-(1,3-dithiolan-2-yl)-5a,8-dimethyl-4-phenyl-2,5a,8,8a-tetrahydro-1H-cyclopenta[4,5]furo[3,2-c]pyridin-1-one