(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

Base Information

Chemical Name:(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
CAS No.:1450732-94-1
Molecular Formula:C₂₈H₄₅NO₈Si
Molecular Weight:551.753
Hs Code.:

Synonyms:(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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (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

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Technology Process of (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

There total 17 articles about (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 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: 88.0%

: 1450732-89-4
(4S)-4-[(1'R,2'R,3'R,4'R)-3'-[(tert-butyldimethylsilyl)oxy]-1',2':4',5'-bis(isopropylidenedioxy)pentyl]oxazolidin-2-one

: 824-94-2
p-methoxybenzyl chloride

: 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

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 0.666667h; Inert atmosphere;
DOI:10.1016/j.tet.2013.07.028

Reference yield:

: C₂₀H₃₉NO₅Si

: 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

Guidance literature:: Multi-step reaction with 5 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

With sodium tetrahydroborate; 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

: 1450732-94-1
(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

Guidance literature:: Multi-step reaction with 6 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

With sodium tetrahydroborate; 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