(1R,4R,5S)-2-oxo-4-hydroxy-7-benzyloxycarbonyl-3,7-diazabicyclo[3.3.1]nonane

Base Information

Chemical Name:(1R,4R,5S)-2-oxo-4-hydroxy-7-benzyloxycarbonyl-3,7-diazabicyclo[3.3.1]nonane
CAS No.:251346-89-1
Molecular Formula:C₁₅H₁₈N₂O₄
Molecular Weight:290.319
Hs Code.:

Synonyms:(1R,4R,5S)-2-oxo-4-hydroxy-7-benzyloxycarbonyl-3,7-diazabicyclo[3.3.1]nonane

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Chemical Property of (1R,4R,5S)-2-oxo-4-hydroxy-7-benzyloxycarbonyl-3,7-diazabicyclo[3.3.1]nonane

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Technology Process of (1R,4R,5S)-2-oxo-4-hydroxy-7-benzyloxycarbonyl-3,7-diazabicyclo[3.3.1]nonane

There total 5 articles about (1R,4R,5S)-2-oxo-4-hydroxy-7-benzyloxycarbonyl-3,7-diazabicyclo[3.3.1]nonane 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%

: 251347-00-9
(3R,5S)-3-carboxyamido-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester

: 251346-89-1
(1R,4R,5S)-2-oxo-4-hydroxy-7-benzyloxycarbonyl-3,7-diazabicyclo[3.3.1]nonane

Guidance literature:: With Dess-Martin periodane; In dichloromethane; for 0.166667h;
DOI:10.1016/S0040-4020(99)00674-2

Reference yield:

: 206761-38-8
(3S,5R)-3-acetoxymethyl-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester

: 251346-89-1
(1R,4R,5S)-2-oxo-4-hydroxy-7-benzyloxycarbonyl-3,7-diazabicyclo[3.3.1]nonane

Guidance literature:: Multi-step reaction with 5 steps

1: 75 percent / KMnO₄ / acetone / 3 h / 0 - 20 °C

2: SOCl₂ / 4 h / Heating

3: NH₃ / dioxane / 3 h / 0 °C

4: 92 percent / 0.5N NaOH / tetrahydrofuran / 2 h / 20 °C

5: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.17 h

With sodium hydroxide; potassium permanganate; thionyl chloride; ammonia; Dess-Martin periodane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetone; 1: Oxidation / 2: Chlorination / 3: Substitution / 4: Deacetylation / 5: Oxidation;
DOI:10.1016/S0040-4020(99)00674-2

Reference yield:

: (3S,5R)-3-Acetoxymethyl-5-chlorocarbonyl-piperidine-1-carboxylic acid benzyl ester

: 251346-89-1
(1R,4R,5S)-2-oxo-4-hydroxy-7-benzyloxycarbonyl-3,7-diazabicyclo[3.3.1]nonane

Guidance literature:: Multi-step reaction with 3 steps

1: NH₃ / dioxane / 3 h / 0 °C

2: 92 percent / 0.5N NaOH / tetrahydrofuran / 2 h / 20 °C

3: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.17 h

With sodium hydroxide; ammonia; Dess-Martin periodane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 1: Substitution / 2: Deacetylation / 3: Oxidation;
DOI:10.1016/S0040-4020(99)00674-2