(2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-7-(4-methoxybenzyloxy)-2,4-dimethylheptyl 4-methylbenzenesulfonate

Base Information

Chemical Name:(2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-7-(4-methoxybenzyloxy)-2,4-dimethylheptyl 4-methylbenzenesulfonate
CAS No.:500220-34-8
Molecular Formula:C₃₀H₄₈O₇SSi
Molecular Weight:580.858
Hs Code.:

Synonyms:(2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-7-(4-methoxybenzyloxy)-2,4-dimethylheptyl 4-methylbenzenesulfonate

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Chemical Property of (2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-7-(4-methoxybenzyloxy)-2,4-dimethylheptyl 4-methylbenzenesulfonate

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Technology Process of (2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-7-(4-methoxybenzyloxy)-2,4-dimethylheptyl 4-methylbenzenesulfonate

There total 11 articles about (2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-7-(4-methoxybenzyloxy)-2,4-dimethylheptyl 4-methylbenzenesulfonate 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:

: 866530-02-1
(2S,3R)-N-methoxy-N-methyl-3-hydroxy-5-(4-methoxybenzyloxy)-2-methylpentamide

: 500220-34-8
(2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-7-(4-methoxybenzyloxy)-2,4-dimethylheptyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 5 steps

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

2: 96 percent / tBu₂AlH / tetrahydrofuran; hexane / 0.5 h / -50 °C

3: 91 percent / LiI; O-trimethylsilylquinine; N,N-diisopropylethylamine / CH₂Cl₂; diethyl ether / -78 °C

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

5: 2.05 g / pyridine; DMAP / CH₂Cl₂ / 22 h / 20 °C

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

Reference yield:

: 500220-30-4
(2S,3R)-3-(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2-methylpentanal

: 500220-34-8
(2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-7-(4-methoxybenzyloxy)-2,4-dimethylheptyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / LiI; O-trimethylsilylquinine; N,N-diisopropylethylamine / CH₂Cl₂; diethyl ether / -78 °C

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

3: 2.05 g / pyridine; DMAP / CH₂Cl₂ / 22 h / 20 °C

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

Reference yield:

: 500220-31-5
(2S,3R)-N-methoxy-N-methyl-3-(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2-methylpentamide

: 500220-34-8
(2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-7-(4-methoxybenzyloxy)-2,4-dimethylheptyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / tBu₂AlH / tetrahydrofuran; hexane / 0.5 h / -50 °C

2: 91 percent / LiI; O-trimethylsilylquinine; N,N-diisopropylethylamine / CH₂Cl₂; diethyl ether / -78 °C

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

4: 2.05 g / pyridine; DMAP / CH₂Cl₂ / 22 h / 20 °C

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