methyl (2R,3S)-7-methyl-2'-oxo-1-(phenylsulfonyl)spiro[indoline-3,4'-oxazolidine]-2-yl terephthalate

Base Information

Chemical Name:methyl (2R,3S)-7-methyl-2'-oxo-1-(phenylsulfonyl)spiro[indoline-3,4'-oxazolidine]-2-yl terephthalate
CAS No.:1448344-81-7
Molecular Formula:C₂₆H₂₂N₂O₈S
Molecular Weight:522.535
Hs Code.:

Synonyms:methyl (2R,3S)-7-methyl-2'-oxo-1-(phenylsulfonyl)spiro[indoline-3,4'-oxazolidine]-2-yl terephthalate

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Chemical Property of methyl (2R,3S)-7-methyl-2'-oxo-1-(phenylsulfonyl)spiro[indoline-3,4'-oxazolidine]-2-yl terephthalate

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Technology Process of methyl (2R,3S)-7-methyl-2'-oxo-1-(phenylsulfonyl)spiro[indoline-3,4'-oxazolidine]-2-yl terephthalate

There total 6 articles about methyl (2R,3S)-7-methyl-2'-oxo-1-(phenylsulfonyl)spiro[indoline-3,4'-oxazolidine]-2-yl terephthalate 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:

: 1448344-63-5
C₂₆H₂₂N₂O₈S

: 1448344-81-7
methyl (2R,3S)-7-methyl-2'-oxo-1-(phenylsulfonyl)spiro[indoline-3,4'-oxazolidine]-2-yl terephthalate

: methyl (2S,3R)-7-methyl-2'-oxo-1-(phenylsulfonyl)spiro[indoline-3,4'-oxazolidine]-2-yl terephthalate

Guidance literature:: With (4S,4'S,5R,5'R)-2,2'-(propane-2,2-diyl)bis(4,5-diphenyl-4,5-dihydrooxazole); iron(II) acetate; In toluene; acetonitrile; at 20 ℃; for 12h; Overall yield = 70 %; Overall yield = 16 mg; stereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1021/ol401666e

Reference yield:

: 98-09-9
benzenesulfonyl chloride

: 1448344-81-7
methyl (2R,3S)-7-methyl-2'-oxo-1-(phenylsulfonyl)spiro[indoline-3,4'-oxazolidine]-2-yl terephthalate

: methyl (2S,3R)-7-methyl-2'-oxo-1-(phenylsulfonyl)spiro[indoline-3,4'-oxazolidine]-2-yl terephthalate

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / dichloromethane / 0.5 h / 0 °C

1.2: 0.5 h / 20 °C

2.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C

3.1: acetonitrile / 1 h / 20 °C

3.2: 4 h / 20 °C

4.1: triethylamine / tetrahydrofuran / 1 h / 0 °C

5.1: iron(II) acetate; (4S,4'S,5R,5'R)-2,2'-(propane-2,2-diyl)bis(4,5-diphenyl-4,5-dihydrooxazole) / acetonitrile; toluene / 12 h / 20 °C / Molecular sieve; Inert atmosphere

With sodium tetrahydroborate; (4S,4'S,5R,5'R)-2,2'-(propane-2,2-diyl)bis(4,5-diphenyl-4,5-dihydrooxazole); tetra(n-butyl)ammonium hydrogensulfate; iron(II) acetate; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;
DOI:10.1021/ol401666e

Reference yield:

: 1448345-12-7
C₁₇H₁₆N₂O₅S

: 1448344-81-7
methyl (2R,3S)-7-methyl-2'-oxo-1-(phenylsulfonyl)spiro[indoline-3,4'-oxazolidine]-2-yl terephthalate

: methyl (2S,3R)-7-methyl-2'-oxo-1-(phenylsulfonyl)spiro[indoline-3,4'-oxazolidine]-2-yl terephthalate

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 1 h / 0 °C

2: iron(II) acetate; (4S,4'S,5R,5'R)-2,2'-(propane-2,2-diyl)bis(4,5-diphenyl-4,5-dihydrooxazole) / acetonitrile; toluene / 12 h / 20 °C / Molecular sieve; Inert atmosphere

With (4S,4'S,5R,5'R)-2,2'-(propane-2,2-diyl)bis(4,5-diphenyl-4,5-dihydrooxazole); iron(II) acetate; triethylamine; In tetrahydrofuran; toluene; acetonitrile;
DOI:10.1021/ol401666e