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

Base Information

• Chemical Name: (4S)-4-[(1'R,2'S,3'R,4'R)-3',4',5'-trihydroxy-1',2'-(isopropylidenedioxy)pentyl]-3-(p-methoxybenzyl)oxazolidin-2-one
• CAS No.: 1450732-98-5
• Molecular Formula: C₁₉H₂₇NO₈
• Molecular Weight: 397.425

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 19 articles about (4S)-4-[(1'R,2'S,3'R,4'R)-3',4',5'-trihydroxy-1',2'-(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: 90.0%

(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 (1450732-96-3) → (4S)-4-[(1'R,2'S,3'R,4'R)-3',4',5'-trihydroxy-1',2'-(isopropylidenedioxy)pentyl]-3-(p-methoxybenzyl)oxazolidin-2-one (1450732-98-5)

Guidance literature:

With acetic acid; In water; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1016/j.tet.2013.07.028

Reference yield:

C20H39NO5Si → (4S)-4-[(1'R,2'S,3'R,4'R)-3',4',5'-trihydroxy-1',2'-(isopropylidenedioxy)pentyl]-3-(p-methoxybenzyl)oxazolidin-2-one (1450732-98-5)

Guidance literature:

Multi-step reaction with 7 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

7: acetic acid / water / 15 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 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 → (4S)-4-[(1'R,2'S,3'R,4'R)-3',4',5'-trihydroxy-1',2'-(isopropylidenedioxy)pentyl]-3-(p-methoxybenzyl)oxazolidin-2-one (1450732-98-5)

Guidance literature:

Multi-step reaction with 8 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

8: acetic acid / water / 15 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; acetic acid; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.tet.2013.07.028

upstream raw materials:

C₂₁H₄₀O₈SSi

C₂₂H₄₁NO₆SSi

methyl [(2S,3R,4R,5R,6R)-5-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-3,4:6,7-bis(isopropylidenedioxy)heptan-2-yl]carbamate

ethyl (4R,5R,6R,7R,2E)-6-[(tert-butyldimethylsilyl)oxy]-4,5:7,8-bis(isopropylidenedioxy)oct-2-enoate

Downstream raw materials:

C₁₇H₂₁NO₆

(4S)-4-[(1'R,2'S,3'Z)-1',2'-(isopropylidenedioxy)hexadec-3'-en-1'-yl]-3-(p-methoxybenzyl)oxazolidin-2-one

(4S)-4-[(1'R,2'S,3'E)-1',2'-(isopropylidenedioxy)hexadec-3'-en-1'-yl]-3-(p-methoxybenzyl)oxazolidin-2-one

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