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

Base Information

• Chemical Name: erythro-α,β-methano-N-(methoxycarbonyl)-1-(phenylsulfonyl)-L-tryptophan methyl ester
• CAS No.: 145642-90-6
• Molecular Formula: C₂₁H₂₀N₂O₆S
• Molecular Weight: 428.466
• Mol file: 145642-90-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about erythro-α,β-methano-N-(methoxycarbonyl)-1-(phenylsulfonyl)-L-tryptophan methyl ester 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: 81.0%

Dimethyl 2,3-methano-8-(phenylsulfonyl)-1,2(S),3(S),3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145642-89-3) → erythro-α,β-methano-N-(methoxycarbonyl)-1-(phenylsulfonyl)-L-tryptophan methyl ester (145642-90-6)

Guidance literature:

With trifluoroacetic acid; In chloroform; for 0.5h; Ambient temperature;

DOI:10.1021/jo00094a041

Reference yield:

dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate (136057-11-9) → erythro-α,β-methano-N-(methoxycarbonyl)-1-(phenylsulfonyl)-L-tryptophan methyl ester (145642-90-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C, 60 min then -78 deg C to r.t.

2: 99 percent / MMPP / tetrahydrofuran / 3 h / Ambient temperature

3: 56 percent / NaH, DMSO / 1.) 2.5 h, 2.) r.t., 5 h

4: 81 percent / TFA / CHCl₃ / 0.5 h / Ambient temperature

With sodium hydride; dimethyl sulfoxide; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; chloroform;

DOI:10.1021/jo00094a041

Reference yield:

Dimethyl 2-(phenylseleno)-8-(phenylsulfonyl)-1,2(R),3,3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145642-79-1) → erythro-α,β-methano-N-(methoxycarbonyl)-1-(phenylsulfonyl)-L-tryptophan methyl ester (145642-90-6)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 56 percent / NaH, DMSO / 1.) 2.5 h, 2.) r.t., 5 h

3: 81 percent / TFA / CHCl₃ / 0.5 h / Ambient temperature

With sodium hydride; dimethyl sulfoxide; trifluoroacetic acid; In tetrahydrofuran; chloroform;

DOI:10.1021/jo00094a041

upstream raw materials:

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

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

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

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