(2S,3S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxy-3-(4-methoxybenzyloxy)pentyl 4-methylbenzenesulfonate

Base Information

Chemical Name:(2S,3S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxy-3-(4-methoxybenzyloxy)pentyl 4-methylbenzenesulfonate
CAS No.:1372785-55-1
Molecular Formula:C₃₆H₄₄O₇SSi
Molecular Weight:648.893
Hs Code.:

Synonyms:(2S,3S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxy-3-(4-methoxybenzyloxy)pentyl 4-methylbenzenesulfonate

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Chemical Property of (2S,3S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxy-3-(4-methoxybenzyloxy)pentyl 4-methylbenzenesulfonate

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Technology Process of (2S,3S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxy-3-(4-methoxybenzyloxy)pentyl 4-methylbenzenesulfonate

There total 6 articles about (2S,3S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxy-3-(4-methoxybenzyloxy)pentyl 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: 90.0%

: 1372785-54-0
(2S,3S)-5-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)pentane-1,2-diol

: 98-59-9
p-toluenesulfonyl chloride

: 1372785-55-1
(2S,3S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxy-3-(4-methoxybenzyloxy)pentyl 4-methylbenzenesulfonate

Guidance literature:: With di(n-butyl)tin oxide; triethylamine; In dichloromethane; at 20 ℃; for 0.5h; chemoselective reaction;
DOI:10.1016/j.tetasy.2012.02.009

Reference yield:

: 1372785-52-8
(S)-4-((S)-1-(4-methoxybenzyloxy)but-3-enyl)-2,2-dimethyl-1,3-dioxolane

: 1372785-55-1
(2S,3S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxy-3-(4-methoxybenzyloxy)pentyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: ozone / dichloromethane / 0.25 h / -78 °C

1.2: -78 °C

2.1: sodium tetrahydroborate / methanol / 0 - 20 °C

3.1: 1H-imidazole / dichloromethane / 0 - 20 °C

4.1: copper(II) choride dihydrate / acetonitrile / 0 - 20 °C

5.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 0.5 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; copper(II) choride dihydrate; di(n-butyl)tin oxide; ozone; triethylamine; In methanol; dichloromethane; acetonitrile;
DOI:10.1016/j.tetasy.2012.02.009

Reference yield:

: 1372785-53-9
tert-butyl ((S)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(4-methoxybenzyloxy)propoxy)diphenylsilane

: 1372785-55-1
(2S,3S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxy-3-(4-methoxybenzyloxy)pentyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1: copper(II) choride dihydrate / acetonitrile / 0 - 20 °C

2: di(n-butyl)tin oxide; triethylamine / dichloromethane / 0.5 h / 20 °C

With copper(II) choride dihydrate; di(n-butyl)tin oxide; triethylamine; In dichloromethane; acetonitrile;
DOI:10.1016/j.tetasy.2012.02.009