(1S,2S,6R,7S,9S)-4,4-Dimethyl-8-((R)-1-phenyl-ethyl)-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)-4,4-Dimethyl-8-((R)-1-phenyl-ethyl)-3,5-dioxa-8-aza-tricyclo[5.2.2.0^2,6]undecane-9-carboxylic acid ethyl ester
• CAS No.: 508204-84-0
• Molecular Formula: C₂₁H₂₉NO₄
• Molecular Weight: 359.466
• Mol file: 508204-84-0.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (1S,2S,6R,7S,9S)-4,4-Dimethyl-8-((R)-1-phenyl-ethyl)-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:

2,2-dimethoxy-propane (77-76-9) + ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.2]octane-3-carboxylate (851389-16-7) → (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)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 3h;

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)-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)

Guidance literature:

Multi-step reaction with 2 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

With potassium dioxotetrahydroxoosmate(VI); potassium carbonate; toluene-4-sulfonic acid; potassium hexacyanoferrate(III); In methanol; 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-(2-Benzyloxycarbonylamino-acetyl)-4,4-dimethyl-3,5-dioxa-8-aza-tricyclo[5.2.2.02,6]undecane-9-carboxylic acid ethyl ester (508204-89-5)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 80 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:

2,2-dimethoxy-propane

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

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

Downstream raw materials:

(6S,7S,9aS)-7-Formyl-1-hydroxy-4-oxo-octahydro-pyrido[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

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

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

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