Dimethyl 2-(phenylseleno)-8-(phenylsulfonyl)-1,2(R),3,3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Base Information

Chemical Name:Dimethyl 2-(phenylseleno)-8-(phenylsulfonyl)-1,2(R),3,3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate
CAS No.:145642-79-1
Molecular Formula:C₂₆H₂₄N₂O₆SSe
Molecular Weight:571.512
Hs Code.:

Synonyms:Dimethyl 2-(phenylseleno)-8-(phenylsulfonyl)-1,2(R),3,3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

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Chemical Property of Dimethyl 2-(phenylseleno)-8-(phenylsulfonyl)-1,2(R),3,3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

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Technology Process of Dimethyl 2-(phenylseleno)-8-(phenylsulfonyl)-1,2(R),3,3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

There total 1 articles about Dimethyl 2-(phenylseleno)-8-(phenylsulfonyl)-1,2(R),3,3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate 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: 70.0%

: 5707-04-0
Phenylselenyl chloride

: 136057-11-9
dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate

: 145642-79-1
Dimethyl 2-(phenylseleno)-8-(phenylsulfonyl)-1,2(R),3,3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; 1.) -78 deg C, 30 min, 2.) -78 deg C, 60 min then -78 deg C to r.t.;
DOI:10.1021/jo00094a041

Reference yield: 99.0%

: 145642-79-1
Dimethyl 2-(phenylseleno)-8-(phenylsulfonyl)-1,2(R),3,3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

: 145642-80-4
Dimethyl 8-(phenylsulfonyl)-1,3a(R),8,8a(S)-tetrahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Guidance literature:: With MMPP; In tetrahydrofuran; for 3h; Ambient temperature;
DOI:10.1021/jo00094a041

Reference yield:

: 145642-79-1
Dimethyl 2-(phenylseleno)-8-(phenylsulfonyl)-1,2(R),3,3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

: threo-N-(Methoxycarbonyl)-β-methyl-1-(phenylsulfonyl)-L-tryptophan methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / MMPP / tetrahydrofuran / 3 h / Ambient temperature

2: 1.) lithium 2-thienylcuprate, 2.) TMSCl / 1.) Et₂O, hexane, -70 deg C to -55 deg C, 2.) Et₂O, hexane, THF, -70 deg C to r.t, 4 h

3: 23 percent / LDA / tetrahydrofuran / 1.) -70 deg C, 50 min, 2.) -70 deg C, 5 min

4: 78 percent / MMPP / tetrahydrofuran / 4 h / Ambient temperature

5: 70 percent / H₂ / Pd(OH)2/C / methanol / 60 h / Ambient temperature

6: 93 percent / TFA / 1 h / Ambient temperature

With chloro-trimethyl-silane; lithium 2-thienylcuprate; hydrogen; trifluoroacetic acid; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol;
DOI:10.1021/jo00094a041