3-[2-benzyloxycarbonylamino-2-(4-hydroxy-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-ylcarbamoyl)-ethyl]-indole-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 3-[2-benzyloxycarbonylamino-2-(4-hydroxy-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-ylcarbamoyl)-ethyl]-indole-1-carboxylic acid tert-butyl ester
• CAS No.: 868700-43-0
• Molecular Formula: C₂₉H₃₅N₃O₈S
• Molecular Weight: 585.678

Synonyms:3-[2-benzyloxycarbonylamino-2-(4-hydroxy-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-ylcarbamoyl)-ethyl]-indole-1-carboxylic acid tert-butyl ester

Chemical Property of 3-[2-benzyloxycarbonylamino-2-(4-hydroxy-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-ylcarbamoyl)-ethyl]-indole-1-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of 3-[2-benzyloxycarbonylamino-2-(4-hydroxy-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-ylcarbamoyl)-ethyl]-indole-1-carboxylic acid tert-butyl ester

There total 9 articles about 3-[2-benzyloxycarbonylamino-2-(4-hydroxy-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-ylcarbamoyl)-ethyl]-indole-1-carboxylic acid tert-butyl 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: 89.0%

3-{2-benzyloxycarbonylamino-2-[4-(tert-butyl-dimethyl-silanyloxy)-1,1-dioxo-hexahydro-1λ6-thiopyran-3-ylcarbamoyl]-ethyl}-indole-1-carboxylic acid tert-butyl ester (868700-42-9) → 3-[2-benzyloxycarbonylamino-2-(4-hydroxy-1,1-dioxo-hexahydro-1λ6-thiopyran-3-ylcarbamoyl)-ethyl]-indole-1-carboxylic acid tert-butyl ester (868700-43-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/jo0508954

Reference yield:

tert-Butyl-((3R,4R)-3-isocyanato-tetrahydro-thiopyran-4-yloxy)-dimethyl-silane → 3-[2-benzyloxycarbonylamino-2-(4-hydroxy-1,1-dioxo-hexahydro-1λ6-thiopyran-3-ylcarbamoyl)-ethyl]-indole-1-carboxylic acid tert-butyl ester (868700-43-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / 0 °C

1.2: 3.60 g / tetrahydrofuran; hexane / 0.5 h / 0 - 20 °C

2.1: 74 percent / NaIO₄; KMnO₄; NaHCO₃ / acetone; H₂O / 6 h / 20 °C

3.1: 100 percent / H₂ / Pd/C / methanol / 5 h / 20 °C / 760 Torr

4.1: 86 percent / HBTU; N,N-diisopropylethylamine / dimethylformamide / 2 h / 20 °C

5.1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

With potassium permanganate; sodium periodate; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo0508954

Reference yield:

(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-thiopyran-3-carboxylic acid → 3-[2-benzyloxycarbonylamino-2-(4-hydroxy-1,1-dioxo-hexahydro-1λ6-thiopyran-3-ylcarbamoyl)-ethyl]-indole-1-carboxylic acid tert-butyl ester (868700-43-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diphenylphosphoryl azide; N,N-diisopropylethylamine / toluene / 4 h / 60 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / 0 °C

2.2: 3.60 g / tetrahydrofuran; hexane / 0.5 h / 0 - 20 °C

3.1: 74 percent / NaIO₄; KMnO₄; NaHCO₃ / acetone; H₂O / 6 h / 20 °C

4.1: 100 percent / H₂ / Pd/C / methanol / 5 h / 20 °C / 760 Torr

5.1: 86 percent / HBTU; N,N-diisopropylethylamine / dimethylformamide / 2 h / 20 °C

6.1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

With potassium permanganate; sodium periodate; n-butyllithium; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; water; N,N-dimethyl-formamide; acetone; toluene; 1.1: Curtius rearrangement;

DOI:10.1021/jo0508954

upstream raw materials:

3-{2-benzyloxycarbonylamino-2-[4-(tert-butyl-dimethyl-silanyloxy)-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-ylcarbamoyl]-ethyl}-indole-1-carboxylic acid tert-butyl ester

3-methoxycarbonyltetrahydropyran-4-one

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