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

Base Information

• Chemical Name: 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
• CAS No.: 868700-42-9
• Molecular Formula: C₃₅H₄₉N₃O₈SSi
• Molecular Weight: 699.941

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 8 articles about 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 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: 86.0%

(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,1-dioxo-hexahydro-1λ6-thiopyran-3-ylamine + (S)-2-(((benzyloxy)carbonyl)amino)-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)propanoic acid (131829-26-0) → 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)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/jo0508954

Reference yield:

tert-Butyl-((3R,4R)-3-isocyanato-tetrahydro-thiopyran-4-yloxy)-dimethyl-silane → 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)

Guidance literature:

Multi-step reaction with 4 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

With potassium permanganate; sodium periodate; n-butyllithium; 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-(tert-butyl-dimethyl-silanyloxy)-1,1-dioxo-hexahydro-1λ6-thiopyran-3-ylcarbamoyl]-ethyl}-indole-1-carboxylic acid tert-butyl ester (868700-42-9)

Guidance literature:

Multi-step reaction with 5 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

With potassium permanganate; sodium periodate; n-butyllithium; diphenylphosphoranyl azide; 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:

(S)-2-(((benzyloxy)carbonyl)amino)-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)propanoic acid

3-methoxycarbonyltetrahydropyran-4-one

Downstream raw materials:

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

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