(S)-3-benzyl-4-((4S,5R)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-oxazolidin-2-one

Base Information

Chemical Name:(S)-3-benzyl-4-((4S,5R)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-oxazolidin-2-one
CAS No.:1332640-38-6
Molecular Formula:C₁₇H₂₃NO₆
Molecular Weight:337.373
Hs Code.:

Synonyms:(S)-3-benzyl-4-((4S,5R)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-oxazolidin-2-one

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Chemical Property of (S)-3-benzyl-4-((4S,5R)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-oxazolidin-2-one

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Technology Process of (S)-3-benzyl-4-((4S,5R)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-oxazolidin-2-one

There total 8 articles about (S)-3-benzyl-4-((4S,5R)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-oxazolidin-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: 96.0%

: 1332640-37-5
3-benzyl-4-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)oxazolidin-2-one

: 1332640-38-6
(S)-3-benzyl-4-((4S,5R)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-oxazolidin-2-one

Guidance literature:: 3-benzyl-4-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)oxazolidin-2-one; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 2h;

With water; In tetrahydrofuran;
DOI:10.1016/j.tetlet.2011.07.032

Reference yield:

: 1233851-77-8
C₂₁H₃₅NO₄Si

: 1332640-38-6
(S)-3-benzyl-4-((4S,5R)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: magnesium / tetrahydrofuran

1.2: 2 h / -78 - 20 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: sodium hydrogencarbonate / methanol / 1 h / 0 - 20 °C

3.1: ozone / dichloromethane / 0.5 h / -78 °C

3.2: 0.5 h / -78 °C

4.1: sodium tetrahydroborate / methanol / 2 h / 0 °C

5.1: sodium hydride / tetrahydrofuran; wax / 0.5 h / 0 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; ozone; magnesium; In tetrahydrofuran; methanol; wax; dichloromethane;
DOI:10.1016/j.tetlet.2011.07.032

Reference yield:

: 1332640-35-3
benzyl benzyl((S)-1-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)allyl)carbamate

: 1332640-38-6
(S)-3-benzyl-4-((4S,5R)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: ozone / dichloromethane / 0.5 h / -78 °C

1.2: 0.5 h / -78 °C

2.1: sodium tetrahydroborate / methanol / 2 h / 0 °C

3.1: sodium hydride / tetrahydrofuran; wax / 0.5 h / 0 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; sodium hydride; ozone; In tetrahydrofuran; methanol; wax; dichloromethane;
DOI:10.1016/j.tetlet.2011.07.032