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

Base Information

Chemical Name:ethyl (1S,3S,4S,5S,6R)-2-(2-benzyloxycarbonylaminoacetyl)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylate
CAS No.:508204-96-4
Molecular Formula:C₂₀H₂₆N₂O₇
Molecular Weight:406.436
Hs Code.:

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

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

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

There total 6 articles about ethyl (1S,3S,4S,5S,6R)-2-(2-benzyloxycarbonylaminoacetyl)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylate 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: 71.0%

: 1138-80-3
N-(Benzyloxycarbonyl)glycine

: 508205-07-0,697289-68-2
ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylate

: 508204-96-4
ethyl (1S,3S,4S,5S,6R)-2-(2-benzyloxycarbonylaminoacetyl)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylate

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:

: 134984-64-8
exo-2-aza-2-<(R)-1-phenylethyl>-3-ethoxycarbonyl<2.2.2>bicyclooct-5-ene

: 508204-96-4
ethyl (1S,3S,4S,5S,6R)-2-(2-benzyloxycarbonylaminoacetyl)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: K₃Fe(CN)6; K₂CO₃; K₂OsO₂(OH)4 / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

2: 18.8 g / H₂ / Pd/C / ethanol / 24 h / 20 °C / 760 Torr

3: 71 percent / HOBt; DCC / dimethylformamide / 12 h / 20 °C

With potassium dioxotetrahydroxoosmate(VI); hydrogen; potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; potassium hexacyanoferrate(III); palladium on activated charcoal; In ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/ejoc.200300700

Reference yield:

: 851389-16-7
ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.2]octane-3-carboxylate

: 508204-96-4
ethyl (1S,3S,4S,5S,6R)-2-(2-benzyloxycarbonylaminoacetyl)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 18.8 g / H₂ / Pd/C / ethanol / 24 h / 20 °C / 760 Torr

2: 71 percent / HOBt; DCC / dimethylformamide / 12 h / 20 °C

With hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300700