(1S,2S,6R,7S,9S)-8-((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-4,4-dimethyl-3,5-dioxa-8-aza-tricyclo[5.2.2.0^2,6]undecane-9-carboxylic acid ethyl ester

Base Information

• Chemical Name: (1S,2S,6R,7S,9S)-8-((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-4,4-dimethyl-3,5-dioxa-8-aza-tricyclo[5.2.2.0^2,6]undecane-9-carboxylic acid ethyl ester
• CAS No.: 508204-92-0
• Molecular Formula: C₂₆H₃₆N₂O₇
• Molecular Weight: 488.581

Synonyms:(1S,2S,6R,7S,9S)-8-((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-4,4-dimethyl-3,5-dioxa-8-aza-tricyclo[5.2.2.0^2,6]undecane-9-carboxylic acid ethyl ester

Chemical Property of (1S,2S,6R,7S,9S)-8-((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-4,4-dimethyl-3,5-dioxa-8-aza-tricyclo[5.2.2.0^2,6]undecane-9-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (1S,2S,6R,7S,9S)-8-((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-4,4-dimethyl-3,5-dioxa-8-aza-tricyclo[5.2.2.0^2,6]undecane-9-carboxylic acid ethyl ester

There total 4 articles about (1S,2S,6R,7S,9S)-8-((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-4,4-dimethyl-3,5-dioxa-8-aza-tricyclo[5.2.2.0^2,6]undecane-9-carboxylic acid ethyl 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: 82.0%

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) + (1S,2S,6R,7S,9S)-4,4-Dimethyl-3,5-dioxa-8-aza-tricyclo[5.2.2.02,6]undecane-9-carboxylic acid ethyl ester (508204-87-3) → (1S,2S,6R,7S,9S)-8-((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-4,4-dimethyl-3,5-dioxa-8-aza-tricyclo[5.2.2.02,6]undecane-9-carboxylic acid ethyl ester (508204-92-0)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1055/s-2002-34901

Reference yield:

exo-2-aza-2-<(R)-1-phenylethyl>-3-ethoxycarbonyl<2.2.2>bicyclooct-5-ene (134984-64-8) → (1S,2S,6R,7S,9S)-8-((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-4,4-dimethyl-3,5-dioxa-8-aza-tricyclo[5.2.2.02,6]undecane-9-carboxylic acid ethyl ester (508204-92-0)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂OsO₂(OH)4; K₃Fe(CN)6; aq. K₂CO₃ / 2-methyl-propan-2-ol / 12 h / 20 °C

2: PTSA / methanol / 3 h / 20 °C

3: 98 percent / H₂ / 5 percent Pd/C / ethanol / 24 h / 20 °C / 760 Torr

4: 82 percent / DCC; HOBt / dimethylformamide / 12 h / 20 °C

With potassium dioxotetrahydroxoosmate(VI); hydrogen; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; potassium hexacyanoferrate(III); palladium on activated charcoal; In methanol; ethanol; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1055/s-2002-34901

Reference yield:

(1S,2S,6R,7S,9S)-4,4-Dimethyl-8-((R)-1-phenyl-ethyl)-3,5-dioxa-8-aza-tricyclo[5.2.2.02,6]undecane-9-carboxylic acid ethyl ester (508204-84-0) → (1S,2S,6R,7S,9S)-8-((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-4,4-dimethyl-3,5-dioxa-8-aza-tricyclo[5.2.2.02,6]undecane-9-carboxylic acid ethyl ester (508204-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / H₂ / 5 percent Pd/C / ethanol / 24 h / 20 °C / 760 Torr

2: 82 percent / DCC; HOBt / dimethylformamide / 12 h / 20 °C

With hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1055/s-2002-34901

upstream raw materials:

(S)-N-(benzyloxycarbonyl)valine

(1S,2S,6R,7S,9S)-4,4-Dimethyl-3,5-dioxa-8-aza-tricyclo[5.2.2.0^2,6]undecane-9-carboxylic acid ethyl ester

exo-2-aza-2-<(R)-1-phenylethyl>-3-ethoxycarbonyl<2.2.2>bicyclooct-5-ene

ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.2]octane-3-carboxylate

Downstream raw materials:

ethyl (1S,3S,4S,5S,6R)-2-[(2S)-2-benzyloxycarbonylamino-3-methylbutyryl]-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylate

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