(+)-(4S,5S)-4-{(1S,2R)-1,2-dibenzyloxy-3-[tert-butyldimethylsilyloxy]propyl}-5-ethynyloxazolidin-2-one

Base Information

Chemical Name:(+)-(4S,5S)-4-{(1S,2R)-1,2-dibenzyloxy-3-[tert-butyldimethylsilyloxy]propyl}-5-ethynyloxazolidin-2-one
CAS No.:1349097-43-3
Molecular Formula:C₂₈H₃₇NO₅Si
Molecular Weight:495.691
Hs Code.:

Synonyms:(+)-(4S,5S)-4-{(1S,2R)-1,2-dibenzyloxy-3-[tert-butyldimethylsilyloxy]propyl}-5-ethynyloxazolidin-2-one

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Chemical Property of (+)-(4S,5S)-4-{(1S,2R)-1,2-dibenzyloxy-3-[tert-butyldimethylsilyloxy]propyl}-5-ethynyloxazolidin-2-one

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Technology Process of (+)-(4S,5S)-4-{(1S,2R)-1,2-dibenzyloxy-3-[tert-butyldimethylsilyloxy]propyl}-5-ethynyloxazolidin-2-one

There total 9 articles about (+)-(4S,5S)-4-{(1S,2R)-1,2-dibenzyloxy-3-[tert-butyldimethylsilyloxy]propyl}-5-ethynyloxazolidin-2-one 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: 43.0%

: 24424-99-5
di-tert-butyl dicarbonate

: (-)-(SS,2S,3R,4S,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide

: 1349097-43-3
(+)-(4S,5S)-4-{(1S,2R)-1,2-dibenzyloxy-3-[tert-butyldimethylsilyloxy]propyl}-5-ethynyloxazolidin-2-one

Guidance literature:: (-)-(SS,2S,3R,4S,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide; With hydrogenchloride; In 1,4-dioxane; methanol; for 2h; Reflux;

di-tert-butyl dicarbonate; With triethylamine; In 1,4-dioxane; methanol; for 2h; Further stages; Reflux;
DOI:10.1021/ol202747p

Reference yield: 26.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 1349097-42-2
(+)-(RS,2S,3R,4S,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide

: 1349097-43-3
(+)-(4S,5S)-4-{(1S,2R)-1,2-dibenzyloxy-3-[tert-butyldimethylsilyloxy]propyl}-5-ethynyloxazolidin-2-one

Guidance literature:: (+)-(RS,2S,3R,4S,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide; With hydrogenchloride; In 1,4-dioxane; methanol; for 2h; Reflux;

di-tert-butyl dicarbonate; With triethylamine; In 1,4-dioxane; methanol; for 2h; Further stages; Reflux;
DOI:10.1021/ol202747p

Reference yield:

: 100-39-0
benzyl bromide

: 1349097-43-3
(+)-(4S,5S)-4-{(1S,2R)-1,2-dibenzyloxy-3-[tert-butyldimethylsilyloxy]propyl}-5-ethynyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: calcium sulfate; silver(l) oxide / acetonitrile / 48 h / 20 °C / Darkness

2.1: trimethylaluminum / tetrahydrofuran; toluene / 0.5 h / 0 - 20 °C

2.2: 17 h / -15 - 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 0 °C

4.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.5 h / -80 - -78 °C / Inert atmosphere

5.1: titanium(IV) tetraethanolate / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

6.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -95 °C / Inert atmosphere

6.2: 0.08 h / -95 - -80 °C / Inert atmosphere

6.3: 1 h / -80 °C / Inert atmosphere

7.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / Reflux

7.2: 2 h / Reflux

With 1H-imidazole; hydrogenchloride; titanium(IV) tetraethanolate; calcium sulfate; trimethylaluminum; tert.-butyl lithium; diisobutylaluminium hydride; silver(l) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; toluene; acetonitrile; pentane;
DOI:10.1021/ol202747p