2-[(1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-isopropenyl-2-methyl-cyclopentyl]-ethanol

Base Information

Chemical Name:2-[(1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-isopropenyl-2-methyl-cyclopentyl]-ethanol
CAS No.:153142-77-9
Molecular Formula:C₂₈H₄₀O₂Si
Molecular Weight:436.71
Hs Code.:

Synonyms:2-[(1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-isopropenyl-2-methyl-cyclopentyl]-ethanol

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Chemical Property of 2-[(1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-isopropenyl-2-methyl-cyclopentyl]-ethanol

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Technology Process of 2-[(1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-isopropenyl-2-methyl-cyclopentyl]-ethanol

There total 12 articles about 2-[(1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-isopropenyl-2-methyl-cyclopentyl]-ethanol 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: 92.0%

: ((1R,4aS,5S,7aR)-1-Bromomethyl-1,5-dimethyl-octahydro-cyclopenta[c]pyran-5-ylmethoxy)-tert-butyl-diphenyl-silane

: 153142-77-9
2-[(1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-isopropenyl-2-methyl-cyclopentyl]-ethanol

Guidance literature:: With ethanol; ammonium chloride; zinc; Heating;
DOI:10.1021/ja00077a097

Reference yield:

: 98049-46-8
(1'R,2'R)-2-(2'-hydroxymethyl-2'-methyl-3'-methylenecyclopentyl)ethanoic acid

: 153142-77-9
2-[(1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-isopropenyl-2-methyl-cyclopentyl]-ethanol

Guidance literature:: Multi-step reaction with 11 steps

1: Et₃N, AgNO₃ / dimethylformamide

2: LiAlH₄ / CH₂Cl₂ / 0 °C

3: i-Pr₂NEt / CH₂Cl₂ / 0 °C

4: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂

5: 1.) NaN(TMS)2, TMSCl, 2.) Pd(OAc)2 / 1.) THF, -15 deg C, 2.) MeCN, 22 deg C

6: 92 percent / n-BuLi, CuBr*DMS / tetrahydrofuran / -78 °C

7: 88 percent / NBS / tetrahydrofuran / 0 - 22 °C

8: 88 percent / DIBAL / CH₂Cl₂ / -78 °C

9: 85 percent / Imd₂C=S, DMAP / various solvent(s) / 22 - 180 °C

10: 99 percent / TsNHNH₂, NaOAc / tetrahydrofuran; H₂O / 75 °C

11: 92 percent / Zn, EtOH, NH₄Cl / Heating

With dmap; palladium diacetate; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; ethanol; sodium acetate; sodium hexamethyldisilazane; diisobutylaluminium hydride; ammonium chloride; ozone; silver nitrate; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1'-Thiocarbonyldiimidazole; toluene-4-sulfonic acid hydrazide; triphenylphosphine; zinc; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00077a097

Reference yield:

: 122552-73-2
C₄₂H₅₂O₃Si₂

: 153142-77-9
2-[(1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-isopropenyl-2-methyl-cyclopentyl]-ethanol

Guidance literature:: Multi-step reaction with 10 steps

1: LiAlH₄ / CH₂Cl₂ / 0 °C

2: i-Pr₂NEt / CH₂Cl₂ / 0 °C

3: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂

4: 1.) NaN(TMS)2, TMSCl, 2.) Pd(OAc)2 / 1.) THF, -15 deg C, 2.) MeCN, 22 deg C

5: 92 percent / n-BuLi, CuBr*DMS / tetrahydrofuran / -78 °C

6: 88 percent / NBS / tetrahydrofuran / 0 - 22 °C

7: 88 percent / DIBAL / CH₂Cl₂ / -78 °C

8: 85 percent / Imd₂C=S, DMAP / various solvent(s) / 22 - 180 °C

9: 99 percent / TsNHNH₂, NaOAc / tetrahydrofuran; H₂O / 75 °C

10: 92 percent / Zn, EtOH, NH₄Cl / Heating

With dmap; palladium diacetate; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; ethanol; sodium acetate; sodium hexamethyldisilazane; diisobutylaluminium hydride; ammonium chloride; ozone; N-ethyl-N,N-diisopropylamine; 1,1'-Thiocarbonyldiimidazole; toluene-4-sulfonic acid hydrazide; triphenylphosphine; zinc; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ja00077a097