tert-butyl-{(S)-1-[2-(4-methoxy-benzyloxy)-1,1-dimethyl-ethyl]-pent-4-enyloxy}-dimethyl-silane

Base Information

• Chemical Name: tert-butyl-{(S)-1-[2-(4-methoxy-benzyloxy)-1,1-dimethyl-ethyl]-pent-4-enyloxy}-dimethyl-silane
• CAS No.: 1312554-79-2
• Molecular Formula: C₂₃H₄₀O₃Si
• Molecular Weight: 392.654

Synonyms:tert-butyl-{(S)-1-[2-(4-methoxy-benzyloxy)-1,1-dimethyl-ethyl]-pent-4-enyloxy}-dimethyl-silane

Chemical Property of tert-butyl-{(S)-1-[2-(4-methoxy-benzyloxy)-1,1-dimethyl-ethyl]-pent-4-enyloxy}-dimethyl-silane

Chemical Property:

Purity/Quality:

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Technology Process of tert-butyl-{(S)-1-[2-(4-methoxy-benzyloxy)-1,1-dimethyl-ethyl]-pent-4-enyloxy}-dimethyl-silane

There total 2 articles about tert-butyl-{(S)-1-[2-(4-methoxy-benzyloxy)-1,1-dimethyl-ethyl]-pent-4-enyloxy}-dimethyl-silane 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: 100.0%

(S)-1-(4-methoxy-benzyloxy)-2,2-dimethyl-hept-6-en-3-ol (1312554-86-1) + t-butyldimethylsiyl triflate (69739-34-0) → tert-butyl-{(S)-1-[2-(4-methoxy-benzyloxy)-1,1-dimethyl-ethyl]-pent-4-enyloxy}-dimethyl-silane (1312554-79-2)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol201336x

Reference yield:

(2R)-1,2-epoxy-4-(p-methoxyphenyl)methoxy-3,3-dimethylbutane (135304-49-3) → tert-butyl-{(S)-1-[2-(4-methoxy-benzyloxy)-1,1-dimethyl-ethyl]-pent-4-enyloxy}-dimethyl-silane (1312554-79-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: copper(l) iodide / tetrahydrofuran / -20 °C / Inert atmosphere

1.2: -20 - 0 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; copper(l) iodide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol201336x

Reference yield:

tert-butyl-{(S)-1-[2-(4-methoxy-benzyloxy)-1,1-dimethyl-ethyl]-pent-4-enyloxy}-dimethyl-silane (1312554-79-2) → (S)-7-((S)-5-benzyloxy-3-methyl-pentyl)-5,6-bis(bromomethyl)-1,1-dimethyl-1,2,3,4-tetrahydro-naphthalen-2-ol (1312554-85-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 °C / pH 7 / Inert atmosphere; aq. buffer

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 0 °C / Inert atmosphere

3.1: potassium carbonate / methanol / 16 h / 20 °C / Inert atmosphere

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 18 h / 50 °C / Inert atmosphere

4.2: 10 h / 110 °C / Inert atmosphere

4.3: Inert atmosphere

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

6.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium aluminium tetrahydride; oxalyl dichloride; carbon tetrabromide; potassium carbonate; dimethyl sulfoxide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; toluene; 2.1: Swern oxidation / 2.2: Swern oxidation;

DOI:10.1021/ol201336x

upstream raw materials:

(S)-1-(4-methoxy-benzyloxy)-2,2-dimethyl-hept-6-en-3-ol

t-butyldimethylsiyl triflate

(2R)-1,2-epoxy-4-(p-methoxyphenyl)methoxy-3,3-dimethylbutane

Downstream raw materials:

[(S)-3-((E)-(S)-7-benzyloxy-5-methyl-hept-1-enyl)-2,2-dimethyl-cyclohex-3-enyloxy]-tert-butyl-dimethyl-silane

(S)-3-((S)-5-benzyloxy-3-methyl-pentyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalene-1,2-dicarboxylic acid

[(S)-3-((S)-5-benzyloxy-3-methyl-pentyl)-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-1-yl]-methanol

(S)-7-((S)-5-benzyloxy-3-methyl-pentyl)-5,6-bis(bromomethyl)-1,1-dimethyl-1,2,3,4-tetrahydro-naphthalen-2-ol

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