(4S)-4-[(1'R,2'S,3'R,4'R)-3'-hydroxy-1',2':4',5'-bis(isopropylidenedioxy) pentyl]-3-(p-methoxybenzyl)oxazolidin-2-one

Base Information

Chemical Name:(4S)-4-[(1'R,2'S,3'R,4'R)-3'-hydroxy-1',2':4',5'-bis(isopropylidenedioxy) pentyl]-3-(p-methoxybenzyl)oxazolidin-2-one
CAS No.:1450732-96-3
Molecular Formula:C₂₂H₃₁NO₈
Molecular Weight:437.49
Hs Code.:

Synonyms:(4S)-4-[(1'R,2'S,3'R,4'R)-3'-hydroxy-1',2':4',5'-bis(isopropylidenedioxy) pentyl]-3-(p-methoxybenzyl)oxazolidin-2-one

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Chemical Property of (4S)-4-[(1'R,2'S,3'R,4'R)-3'-hydroxy-1',2':4',5'-bis(isopropylidenedioxy) pentyl]-3-(p-methoxybenzyl)oxazolidin-2-one

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Technology Process of (4S)-4-[(1'R,2'S,3'R,4'R)-3'-hydroxy-1',2':4',5'-bis(isopropylidenedioxy) pentyl]-3-(p-methoxybenzyl)oxazolidin-2-one

There total 18 articles about (4S)-4-[(1'R,2'S,3'R,4'R)-3'-hydroxy-1',2':4',5'-bis(isopropylidenedioxy) pentyl]-3-(p-methoxybenzyl)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: 93.0%

: 1450732-94-1
(4S)-4-[(1'R,2'R,3'R,4'R)-3'-[(tert-butyldimethylsilyl)oxy]-1',2':4',5'-bis(isopropylidenedioxy)pentyl]-3-(p-methoxybenzyl)oxazolidin-2-one

: 1450732-96-3
(4S)-4-[(1'R,2'S,3'R,4'R)-3'-hydroxy-1',2':4',5'-bis(isopropylidenedioxy) pentyl]-3-(p-methoxybenzyl)oxazolidin-2-one

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 0.666667h; Inert atmosphere;
DOI:10.1016/j.tet.2013.07.028

Reference yield:

: C₂₀H₃₉NO₅Si

: 1450732-96-3
(4S)-4-[(1'R,2'S,3'R,4'R)-3'-hydroxy-1',2':4',5'-bis(isopropylidenedioxy) pentyl]-3-(p-methoxybenzyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: triethylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere

2: ozone / methanol; dichloromethane / 0.25 h / -78 °C

3: sodium tetrahydroborate / methanol; dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere

4: sodium hydride / tetrahydrofuran; mineral oil / 48.3 h / 0 - 20 °C / Inert atmosphere

5: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; mineral oil / 0.67 h / 0 - 20 °C / Inert atmosphere

6: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.67 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.tet.2013.07.028

Reference yield:

: N-{(4′R,5′R,6′R,7′R)-6′-[(tert-butyldimethylsilyl)oxy]-4′,5′:7′,8′-bis(isopropylidenedioxy)oct-1′-en-3′-yl}-2,2,2-trichloroacetamide

: 1450732-96-3
(4S)-4-[(1'R,2'S,3'R,4'R)-3'-hydroxy-1',2':4',5'-bis(isopropylidenedioxy) pentyl]-3-(p-methoxybenzyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: sodium hydroxide / water; ethanol / 5 h / 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere

3: ozone / methanol; dichloromethane / 0.25 h / -78 °C

4: sodium tetrahydroborate / methanol; dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere

5: sodium hydride / tetrahydrofuran; mineral oil / 48.3 h / 0 - 20 °C / Inert atmosphere

6: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; mineral oil / 0.67 h / 0 - 20 °C / Inert atmosphere

7: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.67 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.tet.2013.07.028