Dimethyl 2-(phenylthio)-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-(phenylthio)-8-(phenylsulfonyl)-1,2(R),3,3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate
• CAS No.: 160579-28-2
• Molecular Formula: C₂₆H₂₄N₂O₆S₂
• Molecular Weight: 524.618
• Mol file: 160579-28-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Dimethyl 2-(phenylthio)-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-(phenylthio)-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: 76.0%

dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate (136057-11-9) + diphenyldisulfane (882-33-7) → Dimethyl 2-(phenylthio)-8-(phenylsulfonyl)-1,2(R),3,3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (160579-28-2)

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: 72.0%

Dimethyl 2-(phenylthio)-8-(phenylsulfonyl)-1,2(R),3,3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (160579-28-2) → Dimethyl 8-(phenylsulfonyl)-1,3a(R),8,8a(S)-tetrahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145642-80-4) + (2R,3aR,8aS)-8-Benzenesulfonyl-2-methoxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester

Guidance literature:

With methanol; In tetrahydrofuran; 1.) 0 deg C to r.t., 2.) r.t, overnight;

DOI:10.1021/jo00094a041

Reference yield: 72.0%

methanol (67-56-1) + Dimethyl 2-(phenylthio)-8-(phenylsulfonyl)-1,2(R),3,3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (160579-28-2) → Dimethyl 8-(phenylsulfonyl)-1,3a(R),8,8a(S)-tetrahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145642-80-4) + (2R,3aR,8aS)-8-Benzenesulfonyl-2-methoxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester

Guidance literature:

With MMPP; In tetrahydrofuran; Title compound not separated from byproducts; 1.) 0 deg C to r.t., 2.) r.t, overnight;

DOI:10.1021/jo00094a041

upstream raw materials:

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

diphenyldisulfane

Downstream raw materials:

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

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

erythro-α,β-methano-N-(methoxycarbonyl)-1-(phenylsulfonyl)-L-tryptophan methyl ester

erythro-β-n-Butyl-N-(methoxycarbonyl)-1-(phenylsulfonyl)-L-tryptophan methyl ester