(3R,14S)-3,14-Bis-(tert-butyl-dimethyl-silanyloxy)-16-(4-methoxy-benzyloxy)-7-oxo-hexadec-10-ynal

Base Information

Chemical Name:(3R,14S)-3,14-Bis-(tert-butyl-dimethyl-silanyloxy)-16-(4-methoxy-benzyloxy)-7-oxo-hexadec-10-ynal
CAS No.:367501-96-0
Molecular Formula:C₃₆H₆₂O₆Si₂
Molecular Weight:647.056
Hs Code.:

Synonyms:(3R,14S)-3,14-Bis-(tert-butyl-dimethyl-silanyloxy)-16-(4-methoxy-benzyloxy)-7-oxo-hexadec-10-ynal

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Chemical Property of (3R,14S)-3,14-Bis-(tert-butyl-dimethyl-silanyloxy)-16-(4-methoxy-benzyloxy)-7-oxo-hexadec-10-ynal

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Technology Process of (3R,14S)-3,14-Bis-(tert-butyl-dimethyl-silanyloxy)-16-(4-methoxy-benzyloxy)-7-oxo-hexadec-10-ynal

There total 6 articles about (3R,14S)-3,14-Bis-(tert-butyl-dimethyl-silanyloxy)-16-(4-methoxy-benzyloxy)-7-oxo-hexadec-10-ynal 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: 99.0%

: 367502-01-0
(3R,14S)-3,14-Bis-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-16-(4-methoxy-benzyloxy)-hexadec-10-yn-7-one

: 367501-96-0
(3R,14S)-3,14-Bis-(tert-butyl-dimethyl-silanyloxy)-16-(4-methoxy-benzyloxy)-7-oxo-hexadec-10-ynal

Guidance literature:: With dimethyl pimelimidate dihydrochloride; sodium hydrogencarbonate; In dichloromethane; at 23 ℃; for 20h;
DOI:10.1039/b104200a

Reference yield:

: 8-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-dec-4-ynal

: 367501-96-0
(3R,14S)-3,14-Bis-(tert-butyl-dimethyl-silanyloxy)-16-(4-methoxy-benzyloxy)-7-oxo-hexadec-10-ynal

Guidance literature:: Multi-step reaction with 5 steps

1.1: BuLi / tetrahydrofuran / 0.5 h / -78 °C

1.2: tetrahydrofuran / 0.5 h / -78 °C

2.1: SmI₂ / tetrahydrofuran; methanol / 0.5 h / 0 °C

2.2: Al(Hg) / tetrahydrofuran; H₂O / 16 h / 23 °C

3.1: 88 percent / PPTS / methanol; CH₂Cl₂ / 10.5 h / 21 °C

4.1: 99 percent / DMPI; NaHCO₃ / CH₂Cl₂ / 20 h / 23 °C

With n-butyllithium; samarium diiodide; dimethyl pimelimidate dihydrochloride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; 2.1: Swern oxidation;
DOI:10.1039/b104200a

Reference yield:

: (4-benzenesulfonyl-1-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-butoxy)-tert-butyl-dimethyl-silane

: 367501-96-0
(3R,14S)-3,14-Bis-(tert-butyl-dimethyl-silanyloxy)-16-(4-methoxy-benzyloxy)-7-oxo-hexadec-10-ynal

Guidance literature:: Multi-step reaction with 5 steps

1.1: BuLi / tetrahydrofuran / 0.5 h / -78 °C

1.2: tetrahydrofuran / 0.5 h / -78 °C

2.1: SmI₂ / tetrahydrofuran; methanol / 0.5 h / 0 °C

2.2: Al(Hg) / tetrahydrofuran; H₂O / 16 h / 23 °C

3.1: 88 percent / PPTS / methanol; CH₂Cl₂ / 10.5 h / 21 °C

4.1: 99 percent / DMPI; NaHCO₃ / CH₂Cl₂ / 20 h / 23 °C

With n-butyllithium; samarium diiodide; dimethyl pimelimidate dihydrochloride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; 2.1: Swern oxidation;
DOI:10.1039/b104200a