(1S,4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-en-1-yl methyl carbonate

Base Information

Chemical Name:(1S,4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-en-1-yl methyl carbonate
CAS No.:1268265-19-5
Molecular Formula:C₂₆H₃₄O₄Si
Molecular Weight:438.639
Hs Code.:

Synonyms:(1S,4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-en-1-yl methyl carbonate

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Chemical Property of (1S,4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-en-1-yl methyl carbonate

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Technology Process of (1S,4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-en-1-yl methyl carbonate

There total 9 articles about (1S,4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-en-1-yl methyl carbonate 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: 99.0%

: 1268265-22-0
(1S,4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-enol

: 79-22-1
methyl chloroformate

: 1268265-19-5
(1S,4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-en-1-yl methyl carbonate

Guidance literature:: With N,N,N,N,-tetramethylethylenediamine; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1021/ol200022a

Reference yield:

: 876152-36-2
(2R,3R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methylcyclopentanone

: 1268265-19-5
(1S,4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-en-1-yl methyl carbonate

Guidance literature:: Multi-step reaction with 5 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

With pyridine; copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; N,N,N,N,-tetramethylethylenediamine; triphenyl-arsane; iodine; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; tetrachloromethane; hexane; dichloromethane; 3.1: Stille coupling;
DOI:10.1021/ol200022a

Reference yield:

: 1268265-20-8
(4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-methylcyclopent-2-enone

: 1268265-19-5
(1S,4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-en-1-yl methyl carbonate

Guidance literature:: Multi-step reaction with 4 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

With pyridine; copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; N,N,N,N,-tetramethylethylenediamine; triphenyl-arsane; iodine; diisobutylaluminium hydride; In 1-methyl-pyrrolidin-2-one; tetrachloromethane; hexane; dichloromethane; 2: Stille coupling;
DOI:10.1021/ol200022a