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

Base Information

Chemical Name:(1S,4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-enol
CAS No.:1268265-22-0
Molecular Formula:C₂₄H₃₂O₂Si
Molecular Weight:380.602
Hs Code.:

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

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

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

There total 8 articles about (1S,4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-enol 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%

: 1268265-21-9
(4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-enone

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

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 1h; stereoselective reaction; Inert atmosphere;
DOI:10.1021/ol200022a

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

With pyridine; copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; 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

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

Guidance literature:: Multi-step reaction with 3 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

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