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

Base Information

Chemical Name:(2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-methoxy-7-(4-methoxybenzyloxy)-2,4-dimethylheptyl 4-methylbenzenesulfonate
CAS No.:500220-29-1
Molecular Formula:C₃₁H₅₀O₇SSi
Molecular Weight:594.885
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 14 articles about (2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-methoxy-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: 89.0%

: 420-37-1
trimethoxonium tetrafluoroborate

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

: 500220-29-1
(2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-methoxy-7-(4-methoxybenzyloxy)-2,4-dimethylheptyl 4-methylbenzenesulfonate

Guidance literature:: With Proton Sponge; In dichloromethane; at 25 ℃;
DOI:10.1021/ol027211o

Reference yield:

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

: 500220-29-1
(2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-methoxy-7-(4-methoxybenzyloxy)-2,4-dimethylheptyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 6 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

6: 81 percent / proton sponge / CH₂Cl₂ / 8 h / 20 °C

With pyridine; 1H-imidazole; dmap; Proton Sponge; (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

: 500220-29-1
(2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-methoxy-7-(4-methoxybenzyloxy)-2,4-dimethylheptyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 4 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

4: 81 percent / proton sponge / CH₂Cl₂ / 8 h / 20 °C

With pyridine; dmap; Proton Sponge; (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