(R)-4-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-1-(4-methoxy-benzyloxy)-3-trimethylsilanyl-prop-2-ynyl]-octanal

Base Information

Chemical Name:(R)-4-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-1-(4-methoxy-benzyloxy)-3-trimethylsilanyl-prop-2-ynyl]-octanal
CAS No.:259656-60-5
Molecular Formula:C₂₈H₄₈O₄Si₂
Molecular Weight:504.858
Hs Code.:

Synonyms:(R)-4-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-1-(4-methoxy-benzyloxy)-3-trimethylsilanyl-prop-2-ynyl]-octanal

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Chemical Property of (R)-4-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-1-(4-methoxy-benzyloxy)-3-trimethylsilanyl-prop-2-ynyl]-octanal

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Technology Process of (R)-4-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-1-(4-methoxy-benzyloxy)-3-trimethylsilanyl-prop-2-ynyl]-octanal

There total 12 articles about (R)-4-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-1-(4-methoxy-benzyloxy)-3-trimethylsilanyl-prop-2-ynyl]-octanal 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: 85.0%

: 259656-79-6
1-[(1S,2R)-2-Butyl-2-(tert-butyl-dimethyl-silanyloxy)-1-trimethylsilanylethynyl-hex-5-enyloxymethyl]-4-methoxy-benzene

: 259656-60-5
(R)-4-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-1-(4-methoxy-benzyloxy)-3-trimethylsilanyl-prop-2-ynyl]-octanal

Guidance literature:: 1-[(1S,2R)-2-Butyl-2-(tert-butyl-dimethyl-silanyloxy)-1-trimethylsilanylethynyl-hex-5-enyloxymethyl]-4-methoxy-benzene; With ozone; In pyridine; methanol; dichloromethane; at -78 ℃; for 0.5h;

With triphenylphosphine; In pyridine; methanol; dichloromethane; at 25 ℃; for 2h; Further stages.;
DOI:10.1021/ol991290v

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 259656-60-5
(R)-4-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-1-(4-methoxy-benzyloxy)-3-trimethylsilanyl-prop-2-ynyl]-octanal

Guidance literature:: Multi-step reaction with 11 steps

1.1: 90 percent / NaH / tetrahydrofuran / 3 h / 0 °C

2.1: 86 percent / Amberlyst 15; H₂O / methanol; tetrahydrofuran / 3 h / 50 °C

3.1: 95 percent / imiodazole / CH₂Cl₂ / 1 h / 0 °C

4.1: 90 percent / oxalyl chloride; dimethylsulfoxide; Et₃N / CH₂Cl₂ / -78 - 25 °C

5.1: Li; sand / diethyl ether / -40 °C

5.2: tetrahydrofuran / 4 h / -78 °C

6.1: 97 percent / TBAF*THF / tetrahydrofuran / 15 h / 25 °C

7.1: SO₃*pyr; Et₃N; DMSO / CH₂Cl₂ / 2 h / 0 °C

8.1: HMPT / tetrahydrofuran / 1 h / -30 °C

9.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 24 h / 25 °C

10.1: 90 percent / n-BuLi / tetrahydrofuran / 7 h / -78 - 25 °C

11.1: O₃ / CH₂Cl₂; methanol; pyridine / 0.5 h / -78 °C

11.2: 85 percent / triphenylphosphine / pyridine; methanol; CH₂Cl₂ / 2 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; Amberlyst 15; oxalyl dichloride; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; water; lithium; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; 1.1: Etherification / 2.1: Hydrolysis / 3.1: Condensation / 4.1: Oxidation / 5.1: Metallation / 5.2: Alkylation / 6.1: Substitution / 7.1: Oxidation / 8.1: Condensation / 9.1: Substitution / 10.1: Substitution / 11.1: ozonolysis / 11.2: Reduction;
DOI:10.1021/ol991290v

Reference yield:

: 259656-67-2
(2S,3R)-2-(4-Methoxy-benzyloxy)-heptane-1,3-diol

: 259656-60-5
(R)-4-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-1-(4-methoxy-benzyloxy)-3-trimethylsilanyl-prop-2-ynyl]-octanal

Guidance literature:: Multi-step reaction with 9 steps

1.1: 95 percent / imiodazole / CH₂Cl₂ / 1 h / 0 °C

2.1: 90 percent / oxalyl chloride; dimethylsulfoxide; Et₃N / CH₂Cl₂ / -78 - 25 °C

3.1: Li; sand / diethyl ether / -40 °C

3.2: tetrahydrofuran / 4 h / -78 °C

4.1: 97 percent / TBAF*THF / tetrahydrofuran / 15 h / 25 °C

5.1: SO₃*pyr; Et₃N; DMSO / CH₂Cl₂ / 2 h / 0 °C

6.1: HMPT / tetrahydrofuran / 1 h / -30 °C

7.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 24 h / 25 °C

8.1: 90 percent / n-BuLi / tetrahydrofuran / 7 h / -78 - 25 °C

9.1: O₃ / CH₂Cl₂; methanol; pyridine / 0.5 h / -78 °C

9.2: 85 percent / triphenylphosphine / pyridine; methanol; CH₂Cl₂ / 2 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; lithium; ozone; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; 1.1: Condensation / 2.1: Oxidation / 3.1: Metallation / 3.2: Alkylation / 4.1: Substitution / 5.1: Oxidation / 6.1: Condensation / 7.1: Substitution / 8.1: Substitution / 9.1: ozonolysis / 9.2: Reduction;
DOI:10.1021/ol991290v