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

Base Information

Chemical Name:(1R,5S,6S)-5,6-O-isopropylidenedioxy-4-oxo-5-[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl-2-cyclohexenyl methansulfonate
CAS No.:350482-14-3
Molecular Formula:C₂₁H₂₅NO₁₀S₂
Molecular Weight:515.562
Hs Code.:

Synonyms:(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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Chemical Property of (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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Technology Process of (1R,5S,6S)-5,6-O-isopropylidenedioxy-4-oxo-5-[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl-2-cyclohexenyl methansulfonate

There total 5 articles about (1R,5S,6S)-5,6-O-isopropylidenedioxy-4-oxo-5-[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl-2-cyclohexenyl methansulfonate 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: 83.0%

: 124-63-0
methanesulfonyl chloride

: 350482-13-2
(4R,5S,6S)-4-hydroxy-5,6-O-isopropylidenedioxy-6-[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl-2-cyclohexen-1-one

: 350482-14-3
(1R,5S,6S)-5,6-O-isopropylidenedioxy-4-oxo-5-[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl-2-cyclohexenyl methansulfonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1016/j.tet.2005.10.082

Reference yield:

: 350482-09-6
(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

: 350482-14-3
(1R,5S,6S)-5,6-O-isopropylidenedioxy-4-oxo-5-[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl-2-cyclohexenyl methansulfonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: hydrochloric acid / tetrahydrofuran / 6 h / 55 °C

1.2: 67 percent / pyridine / tetrahydrofuran / 2 h / 20 °C

2.1: 74 percent / iodotrimethylsilane / CCl₄ / 1 h / -20 °C

3.1: 95 percent / zinc; acetic acid / tetrahydrofuran; methanol / 1 h / 60 °C

4.1: 59 percent / diphenyl ether / 2 h / 230 °C

5.1: 83 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 20 °C

With hydrogenchloride; dmap; trimethylsilyl iodide; acetic acid; triethylamine; zinc; In tetrahydrofuran; methanol; tetrachloromethane; diphenylether; dichloromethane;
DOI:10.1016/j.tet.2005.10.082

Reference yield:

: 350482-11-0
(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

: 350482-14-3
(1R,5S,6S)-5,6-O-isopropylidenedioxy-4-oxo-5-[(4S)-2-oxo-3-(p-toluenesulfonyl)oxazolidin-4-yl]methyl-2-cyclohexenyl methansulfonate

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 83 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 20 °C

With dmap; acetic acid; triethylamine; zinc; In tetrahydrofuran; methanol; diphenylether; dichloromethane;
DOI:10.1016/j.tet.2005.10.082