(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-O-isopropylidenedioxy-4-[[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl]tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-one

Base Information

• Chemical Name: (1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-O-isopropylidenedioxy-4-[[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl]tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-one
• CAS No.: 350482-10-9
• Molecular Formula: C₂₅H₂₇NO₈S
• Molecular Weight: 501.557

Synonyms:(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-O-isopropylidenedioxy-4-[[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl]tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-one

Chemical Property of (1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-O-isopropylidenedioxy-4-[[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl]tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-one

Chemical Property:

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Technology Process of (1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-O-isopropylidenedioxy-4-[[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl]tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-one

There total 1 articles about (1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-O-isopropylidenedioxy-4-[[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl]tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-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: 67.0%

(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-O-isopropylidenedioxy-4-[[(4R)-2,2-dimethyl-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl]tetracyclo[6.2.1.02,7.02,10]undecan-3-one (350482-09-6) + trichloromethyl chloroformate (503-38-8) → (1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-O-isopropylidenedioxy-4-[[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl]tetracyclo[6.2.1.02,7.02,10]undecan-3-one (350482-10-9)

Guidance literature:

(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-O-isopropylidenedioxy-4-[[(4R)-2,2-dimethyl-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl]tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-one; With hydrogenchloride; In tetrahydrofuran; at 55 ℃; for 6h;

trichloromethyl chloroformate; With pyridine; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2005.10.082

Reference yield: 74.0%

(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-O-isopropylidenedioxy-4-[[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl]tetracyclo[6.2.1.02,7.02,10]undecan-3-one (350482-10-9) → (1S,2S,3S,4R,4aR,5R,6S,7S,8aR)-3,5-epoxy-2-iodo-6,7-O-isopropylidenedioxy-7-[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl-1,2,3,4,4a,5,6,8a-octahydro-endo-1,4-methanonaphthalen-8-one (350482-11-0)

Guidance literature:

With trimethylsilyl iodide; In tetrachloromethane; at -20 ℃; for 1h;

DOI:10.1016/j.tet.2005.10.082

Reference yield:

(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-O-isopropylidenedioxy-4-[[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl]tetracyclo[6.2.1.02,7.02,10]undecan-3-one (350482-10-9) → (4R,5S,6S)-4-hydroxy-5,6-O-isopropylidenedioxy-6-[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl-2-cyclohexen-1-one (350482-13-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / iodotrimethylsilane / CCl₄ / 1 h / -20 °C

2: 95 percent / zinc; acetic acid / tetrahydrofuran; methanol / 1 h / 60 °C

3: 59 percent / diphenyl ether / 2 h / 230 °C

With trimethylsilyl iodide; acetic acid; zinc; In tetrahydrofuran; methanol; tetrachloromethane; diphenylether;

DOI:10.1016/j.tet.2005.10.082

upstream raw materials:

(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-O-isopropylidenedioxy-4-[[(4R)-2,2-dimethyl-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl]tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-one

trichloromethyl chloroformate

Downstream raw materials:

(1S,2S,3S,4R,4aR,5R,6S,7S,8aR)-3,5-epoxy-2-iodo-6,7-O-isopropylidenedioxy-7-[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl-1,2,3,4,4a,5,6,8a-octahydro-endo-1,4-methanonaphthalen-8-one

(4R,5S,6S)-4-hydroxy-5,6-O-isopropylidenedioxy-6-[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl-2-cyclohexen-1-one

(1R,5S,6S)-5,6-dihydroxy-4-oxo-5-[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl-2-cyclohexenyl methansulfonate

(1R,5S,6S)-5,6-O-isopropylidenedioxy-4-oxo-5-[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl-2-cyclohexenyl methansulfonate

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