(2R,3S)-1-((S)-4-benzyl-2-thioxooxazolidin-3-yl)-8-(benzyloxy)-3-hydroxy-2,6,7-trimethyloct-6-en-1-one

Base Information

Chemical Name:(2R,3S)-1-((S)-4-benzyl-2-thioxooxazolidin-3-yl)-8-(benzyloxy)-3-hydroxy-2,6,7-trimethyloct-6-en-1-one
CAS No.:1283712-86-6
Molecular Formula:C₂₉H₃₇NO₅S
Molecular Weight:511.682
Hs Code.:

Synonyms:(2R,3S)-1-((S)-4-benzyl-2-thioxooxazolidin-3-yl)-8-(benzyloxy)-3-hydroxy-2,6,7-trimethyloct-6-en-1-one

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Chemical Property of (2R,3S)-1-((S)-4-benzyl-2-thioxooxazolidin-3-yl)-8-(benzyloxy)-3-hydroxy-2,6,7-trimethyloct-6-en-1-one

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Technology Process of (2R,3S)-1-((S)-4-benzyl-2-thioxooxazolidin-3-yl)-8-(benzyloxy)-3-hydroxy-2,6,7-trimethyloct-6-en-1-one

There total 12 articles about (2R,3S)-1-((S)-4-benzyl-2-thioxooxazolidin-3-yl)-8-(benzyloxy)-3-hydroxy-2,6,7-trimethyloct-6-en-1-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: 60.0%

: 1283712-85-5
(Z)-4,5-dimethyl-6-(para-methoxybenzyloxy)-hex-4-enal

: 145588-95-0,334968-78-4
N-propanoyl-(S)-4-benzyl-1,3-oxazolidine-2-thione

: 1283712-86-6
(2R,3S)-1-((S)-4-benzyl-2-thioxooxazolidin-3-yl)-8-(benzyloxy)-3-hydroxy-2,6,7-trimethyloct-6-en-1-one

Guidance literature:: With titanium tetrachloride; sparteine; In dichloromethane; at -78 - 0 ℃;
DOI:10.1016/j.tetlet.2011.01.093

Reference yield:

: 1283712-84-4
(Z)-(tert-butyldimethylsilanyloxy)-4,5-dimethyl-6-(para-methoxybenzyloxy)-hex-4-ene

: 1283712-86-6
(2R,3S)-1-((S)-4-benzyl-2-thioxooxazolidin-3-yl)-8-(benzyloxy)-3-hydroxy-2,6,7-trimethyloct-6-en-1-one

Guidance literature:: Multi-step reaction with 3 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 25 °C

2: Dess-Martin periodane / dichloromethane / 25 °C

3: titanium tetrachloride; sparteine / dichloromethane / -78 - 0 °C

With tetrabutyl ammonium fluoride; titanium tetrachloride; Dess-Martin periodane; sparteine; In tetrahydrofuran; dichloromethane; 2: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2011.01.093

Reference yield:

: 61362-77-4
5-[tert-butyldimethylsilyloxy]pent-1-yne

: 1283712-86-6
(2R,3S)-1-((S)-4-benzyl-2-thioxooxazolidin-3-yl)-8-(benzyloxy)-3-hydroxy-2,6,7-trimethyloct-6-en-1-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-butyllithium / tetrahydrofuran / -78 °C

2.1: copper(l) iodide / tetrahydrofuran / -45 °C

2.2: -45 - 0 °C

3.1: diisobutylaluminium hydride / dichloromethane / -78 °C

4.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 25 °C

5.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 80 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 25 °C

7.1: Dess-Martin periodane / dichloromethane / 25 °C

8.1: titanium tetrachloride; sparteine / dichloromethane / -78 - 0 °C

With copper(l) iodide; n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; titanium tetrachloride; diisobutylaluminium hydride; Dess-Martin periodane; sparteine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; cyclohexane; 5.1: Negishi cross-coupling reaction / 7.1: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2011.01.093