(4R)-2-(phenylselenyl)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide

Base Information

Chemical Name:(4R)-2-(phenylselenyl)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide
CAS No.:864182-70-7
Molecular Formula:C₂₁H₃₂O₃SeSi
Molecular Weight:439.529
Hs Code.:

Synonyms:(4R)-2-(phenylselenyl)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4R)-2-(phenylselenyl)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide

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Technology Process of (4R)-2-(phenylselenyl)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide

There total 6 articles about (4R)-2-(phenylselenyl)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide 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: 50.0%

: 864182-73-0
(4S)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide

: 34837-55-3
Phenylselenyl bromide

: 864182-70-7
(4R)-2-(phenylselenyl)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide

Guidance literature:: (4S)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.666667h;

Phenylselenyl bromide; In tetrahydrofuran; hexane; at -78 ℃; for 1h;
DOI:10.1039/b504545b

Reference yield:

: 864182-72-9
(4S)-methyl 4-hydroxy-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-enoate

: 864182-70-7
(4R)-2-(phenylselenyl)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide

Guidance literature:: Multi-step reaction with 2 steps

1.1: 91 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 °C

2.1: LDA / tetrahydrofuran; hexane / 0.67 h / -78 °C

2.2: 50 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With lithium diisopropyl amide; In tetrahydrofuran; hexane;
DOI:10.1039/b504545b

Reference yield:

: 85428-31-5
3-(S)-oxiranyl-propionic acid methyl ester

: 864182-70-7
(4R)-2-(phenylselenyl)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide

Guidance literature:: Multi-step reaction with 3 steps

1.1: tBuLi / pentane; tetrahydrofuran / 0.08 h / -78 °C

1.2: CuCN / pentane; tetrahydrofuran / -78 - -60 °C

1.3: 70 percent / BF₃*OEt₂ / tetrahydrofuran; pentane / 1 h / -60 °C

2.1: 91 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 °C

3.1: LDA / tetrahydrofuran; hexane / 0.67 h / -78 °C

3.2: 50 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With tert.-butyl lithium; lithium diisopropyl amide; In tetrahydrofuran; hexane; pentane;
DOI:10.1039/b504545b