3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-hydroxy-1-methyl-hex-5-enyl ester

Base Information

Chemical Name:3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-hydroxy-1-methyl-hex-5-enyl ester
CAS No.:335161-38-1
Molecular Formula:C₂₈H₅₀O₅Si₂
Molecular Weight:522.873
Hs Code.:

Synonyms:3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-hydroxy-1-methyl-hex-5-enyl ester

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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 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-hydroxy-1-methyl-hex-5-enyl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-hydroxy-1-methyl-hex-5-enyl ester

There total 8 articles about 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-hydroxy-1-methyl-hex-5-enyl ester 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: 81.0%

: 866455-75-6
3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-(4-methoxy-benzyloxy)-1-methyl-hex-5-enyl ester

: 335161-38-1
3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-hydroxy-1-methyl-hex-5-enyl ester

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 2h;
DOI:10.1016/j.tetlet.2005.07.075

Reference yield:

: 866455-65-4
1-[(2S)-1,4-dioxaspiro[4,5]dec-2-yl]-4-penten-2-ol

: 335161-38-1
3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-hydroxy-1-methyl-hex-5-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 85 percent / IBX / dimethylsulfoxide; CH₂Cl₂ / 3 h

2.1: 94 percent / LiAlH₄; LiI / diethyl ether; tetrahydrofuran / -100 °C

3.1: 87 percent / NaH / tetrahydrofuran

4.1: 90 percent / PTSA / aq. methanol / 0.5 h / 0 °C

5.1: Et₃N / DMAP / CH₂Cl₂ / 3 h

5.2: 72 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

6.1: 86 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 0 - 20 °C

7.1: 81 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

With dmap; lithium aluminium tetrahydride; sodium hydride; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium iodide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1016/j.tetlet.2005.07.075

Reference yield:

: 866455-67-6
(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-pent-4-en-2-one

: 335161-38-1
3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-hydroxy-1-methyl-hex-5-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 94 percent / LiAlH₄; LiI / diethyl ether; tetrahydrofuran / -100 °C

2.1: 87 percent / NaH / tetrahydrofuran

3.1: 90 percent / PTSA / aq. methanol / 0.5 h / 0 °C

4.1: Et₃N / DMAP / CH₂Cl₂ / 3 h

4.2: 72 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

5.1: 86 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 0 - 20 °C

6.1: 81 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

With dmap; lithium aluminium tetrahydride; sodium hydride; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium iodide; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;
DOI:10.1016/j.tetlet.2005.07.075