(3R,4S,5R,6S)-3-(tert-butyldimethylsilanyloxy)-5-methoxy-1-(4-methoxybenzyloxy)-4,6-dimethyl-9-decene

Base Information

Chemical Name:(3R,4S,5R,6S)-3-(tert-butyldimethylsilanyloxy)-5-methoxy-1-(4-methoxybenzyloxy)-4,6-dimethyl-9-decene
CAS No.:900171-38-2
Molecular Formula:C₂₇H₄₈O₄Si
Molecular Weight:464.761
Hs Code.:

Synonyms:(3R,4S,5R,6S)-3-(tert-butyldimethylsilanyloxy)-5-methoxy-1-(4-methoxybenzyloxy)-4,6-dimethyl-9-decene

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Chemical Property of (3R,4S,5R,6S)-3-(tert-butyldimethylsilanyloxy)-5-methoxy-1-(4-methoxybenzyloxy)-4,6-dimethyl-9-decene

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Technology Process of (3R,4S,5R,6S)-3-(tert-butyldimethylsilanyloxy)-5-methoxy-1-(4-methoxybenzyloxy)-4,6-dimethyl-9-decene

There total 9 articles about (3R,4S,5R,6S)-3-(tert-butyldimethylsilanyloxy)-5-methoxy-1-(4-methoxybenzyloxy)-4,6-dimethyl-9-decene 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:

: 900171-30-4
(3S,4R)-4-[2-(4-methoxybenzyloxy)ethyl]-3-methyloxetan-2-one

: 900171-38-2
(3R,4S,5R,6S)-3-(tert-butyldimethylsilanyloxy)-5-methoxy-1-(4-methoxybenzyloxy)-4,6-dimethyl-9-decene

Guidance literature:: Multi-step reaction with 8 steps

1: dimethylaluminum chloride / CH₂Cl₂; hexane / 2 h / -25 °C

2: imidazole; DMAP / dimethylformamide / 20 h / 20 °C

3: 96 percent / tBu₂AlH / tetrahydrofuran; hexane / 0.5 h / -50 °C

4: 91 percent / LiI; O-trimethylsilylquinine; N,N-diisopropylethylamine / CH₂Cl₂; diethyl ether / -78 °C

5: tBu₂AlH / tetrahydrofuran; hexane / 0.17 h / -50 °C

6: 2.05 g / pyridine; DMAP / CH₂Cl₂ / 22 h / 20 °C

7: 81 percent / proton sponge / CH₂Cl₂ / 8 h / 20 °C

8: 85 percent / CuBr / diethyl ether / -20 - 20 °C

With pyridine; 1H-imidazole; dmap; Proton Sponge; (1S,2R,4S,5R)-2-[(S)-(6-methoxyquinolin-4-yl)((trimethylsilyl)oxy)methyl]-5-vinylquinuclidine; dimethylaluminum chloride; di(tert-butyl)aluminium hydride; N-ethyl-N,N-diisopropylamine; copper(I) bromide; lithium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja061938g

Reference yield:

: 900171-35-9
(3R,4S)-4-[(2S,3R)-2-(tert-butyldimethylsilanyloxy)-4-(4-methoxybenzyloxy)-1-methylbutyl]-3-methyloxetan-2-one

: 900171-38-2
(3R,4S,5R,6S)-3-(tert-butyldimethylsilanyloxy)-5-methoxy-1-(4-methoxybenzyloxy)-4,6-dimethyl-9-decene

Guidance literature:: Multi-step reaction with 4 steps

1: tBu₂AlH / tetrahydrofuran; hexane / 0.17 h / -50 °C

2: 2.05 g / pyridine; DMAP / CH₂Cl₂ / 22 h / 20 °C

3: 81 percent / proton sponge / CH₂Cl₂ / 8 h / 20 °C

4: 85 percent / CuBr / diethyl ether / -20 - 20 °C

With pyridine; dmap; Proton Sponge; di(tert-butyl)aluminium hydride; copper(I) bromide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ja061938g

Reference yield:

: 128461-65-4
3-(p-methoxybenzyloxy)propanal

: 900171-38-2
(3R,4S,5R,6S)-3-(tert-butyldimethylsilanyloxy)-5-methoxy-1-(4-methoxybenzyloxy)-4,6-dimethyl-9-decene

Guidance literature:: Multi-step reaction with 9 steps

1: 70 percent / LiClO₄; O-trimethylsilylquinidine; N,N-diisopropylethylamine / CH₂Cl₂; diethyl ether / 18 h / -78 °C

2: dimethylaluminum chloride / CH₂Cl₂; hexane / 2 h / -25 °C

3: imidazole; DMAP / dimethylformamide / 20 h / 20 °C

4: 96 percent / tBu₂AlH / tetrahydrofuran; hexane / 0.5 h / -50 °C

5: 91 percent / LiI; O-trimethylsilylquinine; N,N-diisopropylethylamine / CH₂Cl₂; diethyl ether / -78 °C

6: tBu₂AlH / tetrahydrofuran; hexane / 0.17 h / -50 °C

7: 2.05 g / pyridine; DMAP / CH₂Cl₂ / 22 h / 20 °C

8: 81 percent / proton sponge / CH₂Cl₂ / 8 h / 20 °C

9: 85 percent / CuBr / diethyl ether / -20 - 20 °C

With pyridine; 1H-imidazole; dmap; Proton Sponge; 2-((1S)-(6-methoxyquinolin-4-yl)((trimethylsilyl)oxy)methyl)5-vinylquinuclidine; (1S,2R,4S,5R)-2-[(S)-(6-methoxyquinolin-4-yl)((trimethylsilyl)oxy)methyl]-5-vinylquinuclidine; lithium perchlorate; dimethylaluminum chloride; di(tert-butyl)aluminium hydride; N-ethyl-N,N-diisopropylamine; copper(I) bromide; lithium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja061938g