(1S,2R,6S,7R)-4-Benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]decane-10-carbaldehyde

Base Information

• Chemical Name: (1S,2R,6S,7R)-4-Benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]decane-10-carbaldehyde
• CAS No.: 214558-26-6
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.353

Synonyms:(1S,2R,6S,7R)-4-Benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]decane-10-carbaldehyde

Chemical Property of (1S,2R,6S,7R)-4-Benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]decane-10-carbaldehyde

Chemical Property:

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Technology Process of (1S,2R,6S,7R)-4-Benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]decane-10-carbaldehyde

There total 4 articles about (1S,2R,6S,7R)-4-Benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]decane-10-carbaldehyde 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: 95.0%

(1R,2R,6S,7S)-4-Benzyloxymethyl-10-[1,3]dithian-2-yl-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione → (1S,2R,6S,7R)-4-Benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]decane-10-carbaldehyde (214558-26-6)

Guidance literature:

With mercury dichloride; mercury(II) oxide; In water; acetonitrile; Heating;

DOI:10.1016/S0040-4039(98)01498-1

Reference yield:

(1R,2R,6S,7S)-4-Benzyloxymethyl-4-aza-tricyclo[5.2.1.02,6]decane-3,5,10-trione (217649-86-0) → (1S,2R,6S,7R)-4-Benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]decane-10-carbaldehyde (214558-26-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / n-BuLi / tetrahydrofuran / -78 °C

2: 95 percent / Et₃SiH, TFA / CH₂Cl₂ / Ambient temperature

3: 95 percent / HgCl₂, HgO / acetonitrile; H₂O / Heating

With triethylsilane; n-butyllithium; trifluoroacetic acid; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(98)01498-1

Reference yield:

(1R,2R,6S,7S)-4-Benzyloxymethyl-10-isopropylidene-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione → (1S,2R,6S,7R)-4-Benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]decane-10-carbaldehyde (214558-26-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / O₃; Me₂S / CH₂Cl₂ / -78 °C

2: 62 percent / n-BuLi / tetrahydrofuran / -78 °C

3: 95 percent / Et₃SiH, TFA / CH₂Cl₂ / Ambient temperature

4: 95 percent / HgCl₂, HgO / acetonitrile; H₂O / Heating

With triethylsilane; n-butyllithium; dimethylsulfide; ozone; trifluoroacetic acid; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(98)01498-1

upstream raw materials:

(1R,2R,6S,7S)-4-Benzyloxymethyl-4-aza-tricyclo[5.2.1.0^2,6]decane-3,5,10-trione

Downstream raw materials:

(1S,2S,6R,7R,10R)-10-Allyl-4-benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]decane-10-carbaldehyde

(1R,2R,6S,7S,10R)-10-Allyl-4-benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]decane-10-carboxylic acid

(1R,2R,6S,7S,10R)-10-Allyl-4-benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]decane-10-carboxylic acid naphthalen-2-yl ester

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