ethyl (1S,2R)-2-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-1-(phenylseleno)cyclopent-3-ene-1-carboxylate

Base Information

Chemical Name:ethyl (1S,2R)-2-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-1-(phenylseleno)cyclopent-3-ene-1-carboxylate
CAS No.:909911-54-2
Molecular Formula:C₂₂H₂₈O₄Se
Molecular Weight:435.422
Hs Code.:

Synonyms:ethyl (1S,2R)-2-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-1-(phenylseleno)cyclopent-3-ene-1-carboxylate

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Chemical Property of ethyl (1S,2R)-2-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-1-(phenylseleno)cyclopent-3-ene-1-carboxylate

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Technology Process of ethyl (1S,2R)-2-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-1-(phenylseleno)cyclopent-3-ene-1-carboxylate

There total 3 articles about ethyl (1S,2R)-2-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-1-(phenylseleno)cyclopent-3-ene-1-carboxylate 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: 63.0%

: 909911-31-5
ethyl (1R,2S)-2-[(2'S)-1',4'-dioxaspiro[4.5]dec-2'-yl]cyclopent-3-ene-1-carboxylate

: 34837-55-3
Phenylselenyl bromide

: 909911-54-2
ethyl (1S,2R)-2-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-1-(phenylseleno)cyclopent-3-ene-1-carboxylate

: ethyl (1R,2R)-2-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-1-(phenylseleno)cyclopent-3-ene-1-carboxylate

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 - -30 ℃; for 2h;
DOI:10.1021/ol061377y

Reference yield:

: ethyl (3S)-2-allyl-3-[(2'S)-1',4'-dioxaspiro[4.5]dec-2'-yl]-pent-4-enoate

: 909911-54-2
ethyl (1S,2R)-2-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-1-(phenylseleno)cyclopent-3-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: (PCy₃)2Cl₂Ru=CHPh / benzene / 36 h / 60 °C

2: 63 percent / LDA; HMPA / tetrahydrofuran; hexane / 2 h / -78 - -30 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; Grubbs catalyst first generation; lithium diisopropyl amide; In tetrahydrofuran; hexane; benzene;
DOI:10.1021/ol061377y

Reference yield:

: 727428-95-7
(3R,2'S)-(1',4'-dioxa-spiro[4.5]dec-2'-yl)-pent-4-enoic acid ethyl ester

: 909911-54-2
ethyl (1S,2R)-2-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-1-(phenylseleno)cyclopent-3-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / LDA; diisopropylamine; HMPA / tetrahydrofuran; hexane / -78 °C

2: (PCy₃)2Cl₂Ru=CHPh / benzene / 36 h / 60 °C

3: 63 percent / LDA; HMPA / tetrahydrofuran; hexane / 2 h / -78 - -30 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; Grubbs catalyst first generation; diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; benzene;
DOI:10.1021/ol061377y