(2S,3aR,8aS)-1-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionyl]-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3aR,8aS)-1-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionyl]-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester
CAS No.:1053271-19-4
Molecular Formula:C₂₉H₃₉N₃O₇Si
Molecular Weight:569.73
Hs Code.:

(2S,3aR,8aS)-1-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionyl]-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

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Chemical Property of (2S,3aR,8aS)-1-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionyl]-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

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Technology Process of (2S,3aR,8aS)-1-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionyl]-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

There total 5 articles about (2S,3aR,8aS)-1-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionyl]-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid 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:

: 2717-76-2,130812-44-1,130812-46-3
(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester

: 1053271-19-4
(2S,3aR,8aS)-1-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionyl]-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / NaOH; Bu₄NHSO₄ / CH₂Cl₂

2: 93 percent / PPTS; Na₂SO₄ / CH₂Cl₂

3: 100 percent / mCPBA; K₂CO₃ / CH₂Cl₂ / 0 - 25 °C

4: 97 percent / TFA / CH₂Cl₂ / 0.08 h

5: 88 percent / H₂ / Pd/C / methanol

6: O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetr; afluorophosphate; NEt₃ / dimethylformamide

With sodium hydroxide; afluorophosphate; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetr; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; potassium carbonate; sodium sulfate; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/b308288a

Reference yield:

: 643751-48-8
3a-hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 1053271-19-4
(2S,3aR,8aS)-1-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionyl]-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 88 percent / H₂ / Pd/C / methanol

2: O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetr; afluorophosphate; NEt₃ / dimethylformamide

With afluorophosphate; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetr; hydrogen; triethylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;
DOI:10.1039/b308288a

Reference yield:

: 643751-46-6
3a-hydroxy-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1-benzyl ester 8-tert-butyl ester 2-methyl ester

: 1053271-19-4
(2S,3aR,8aS)-1-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionyl]-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / TFA / CH₂Cl₂ / 0.08 h

2: 88 percent / H₂ / Pd/C / methanol

3: O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetr; afluorophosphate; NEt₃ / dimethylformamide

With afluorophosphate; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetr; hydrogen; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/b308288a