Acrylic acid (S)-1-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-but-3-enyl ester

Base Information

• Chemical Name: Acrylic acid (S)-1-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-but-3-enyl ester
• CAS No.: 335161-39-2
• Molecular Formula: C₃₁H₅₂O₆Si₂
• Molecular Weight: 576.921

Synonyms:Acrylic acid (S)-1-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-but-3-enyl ester

Chemical Property of Acrylic acid (S)-1-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-but-3-enyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Acrylic acid (S)-1-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-but-3-enyl ester

There total 9 articles about Acrylic acid (S)-1-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-but-3-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:

(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-pent-4-en-2-one (866455-67-6) → Acrylic acid (S)-1-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-but-3-enyl ester (335161-39-2)

Guidance literature:

Multi-step reaction with 7 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

7.1: 70 percent / DMAP / triethylamine / 2 h / 0 - 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; triethylamine;

DOI:10.1016/j.tetlet.2005.07.075

Reference yield:

1-[(2S)-1,4-dioxaspiro[4,5]dec-2-yl]-4-penten-2-ol (866455-65-4) → Acrylic acid (S)-1-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-but-3-enyl ester (335161-39-2)

Guidance literature:

Multi-step reaction with 8 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

8.1: 70 percent / DMAP / triethylamine / 2 h / 0 - 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; triethylamine;

DOI:10.1016/j.tetlet.2005.07.075

Reference yield:

(2S,4S)-4-(4-Methoxy-benzyloxy)-hept-6-ene-1,2-diol (866455-72-3) → Acrylic acid (S)-1-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-but-3-enyl ester (335161-39-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Et₃N / DMAP / CH₂Cl₂ / 3 h

1.2: 72 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

2.1: 86 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 0 - 20 °C

3.1: 81 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

4.1: 70 percent / DMAP / triethylamine / 2 h / 0 - 20 °C

With dmap; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dmap; In dichloromethane; water; triethylamine;

DOI:10.1016/j.tetlet.2005.07.075

upstream raw materials:

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

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

(2R,4S)-4-(4-Methoxy-benzyloxy)-hept-6-en-2-ol

(2S,4S)-4-(4-Methoxy-benzyloxy)-hept-6-ene-1,2-diol

Downstream raw materials:

(R)-1-methyl-2-[(S)-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl 3-(3,4-dihydroxyphenyl)propanoate

(-)-<5(S),7(R)>-7-<5-(oct-2-enolide)-3',4'-bis-(t-butyldimethylsilyloxy)>-dihydrocinnamate

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