2-{3-[(2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]propyl}isoindoline-1,3-dione

Base Information

Chemical Name:2-{3-[(2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]propyl}isoindoline-1,3-dione
CAS No.:887612-26-2
Molecular Formula:C₄₂H₅₅NO₅Si
Molecular Weight:681.988
Hs Code.:

Synonyms:2-{3-[(2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]propyl}isoindoline-1,3-dione

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Chemical Property of 2-{3-[(2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]propyl}isoindoline-1,3-dione

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Technology Process of 2-{3-[(2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]propyl}isoindoline-1,3-dione

There total 18 articles about 2-{3-[(2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]propyl}isoindoline-1,3-dione 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%

: 1391853-35-2
tert-butyl {(S)-4-[(2S,6S,8R,9S)-8-(3-iodopropyl)-9-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]-2-methylbutoxy}diphenylsilane

: 1074-82-4
potassium phtalimide

: 887612-26-2
2-{3-[(2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]propyl}isoindoline-1,3-dione

Guidance literature:: In N,N-dimethyl-formamide; at 40 ℃; for 2.5h; Inert atmosphere;
DOI:10.1002/chem.201102462

Reference yield:

: ((E)-(2S,5S)-5-Benzyloxy-2-methyl-octa-3,7-dienyloxy)-tert-butyl-diphenyl-silane

: 887612-26-2
2-{3-[(2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]propyl}isoindoline-1,3-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: 87 percent / Cl₂(Cy₃P)(IMes)Ru=CHPh / CH₂Cl₂ / 1.5 h / 40 °C

2.1: H₂ / Pd/C / ethyl acetate / 24 h

3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: tetrahydrofuran; hexane / 1.5 h / -78 °C

4.1: 0.746 g / H₂ / Pd/C / ethyl acetate; methanol / 12 h / 2585.74 Torr

5.1: Ph₃P; DEAD / tetrahydrofuran / 2.5 h / 0 °C

With Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; n-butyllithium; hydrogen; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; 5.1: Mitsunobu reaction;
DOI:10.1021/ja057686l

Reference yield:

: (2E,6E)-(5S,8S)-5-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxy)-8-methyl-nona-2,6-dienoic acid methyl ester

: 887612-26-2
2-{3-[(2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]propyl}isoindoline-1,3-dione

Guidance literature:: Multi-step reaction with 4 steps

1.1: H₂ / Pd/C / ethyl acetate / 24 h

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: tetrahydrofuran; hexane / 1.5 h / -78 °C

3.1: 0.746 g / H₂ / Pd/C / ethyl acetate; methanol / 12 h / 2585.74 Torr

4.1: Ph₃P; DEAD / tetrahydrofuran / 2.5 h / 0 °C

With n-butyllithium; hydrogen; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; ethyl acetate; 4.1: Mitsunobu reaction;
DOI:10.1021/ja057686l