(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

Base Information

• Chemical Name: (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
• CAS No.: 350482-09-6
• Molecular Formula: C₂₇H₃₃NO₇S
• Molecular Weight: 515.628

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 1 articles about (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 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: 95.0%

(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](methyldithiocarbonyloxy)-methyl]tetracyclo[6.2.1.02,7.02,10]undecan-3-one → (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)

Guidance literature:

With triethyl borane; tri-n-butyl-tin hydride; In hexane; toluene; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2005.10.082

Reference yield: 80.0%

(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) → C25H31NO7S

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; methanol; at 20 ℃; for 3h;

DOI:10.1021/ol015873s

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

Downstream raw materials:

(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

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

(1S,2S,3S,4R,4aR,5R,6S,7S,8aR)-3,5-epoxy-2-iodo-6,7-O-isopropylidenedioxy-7-[(4S)-2,2-dimethyl-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

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