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

Base Information

• Chemical Name: (1S,2S,6R,7R,10R)-10-Allyl-4-benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]decane-10-carbaldehyde
• CAS No.: 214406-67-4
• Molecular Formula: C₂₁H₂₃NO₄
• Molecular Weight: 353.418

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

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

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

There total 6 articles about (1S,2S,6R,7R,10R)-10-Allyl-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: 75.0%

(1R,2R,6S,7S)-10-[1-Allyloxy-meth-(Z)-ylidene]-4-benzyloxymethyl-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione → (1S,2S,6R,7R,10R)-10-Allyl-4-benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]decane-10-carbaldehyde (214406-67-4)

Guidance literature:

In xylene; for 96h; Heating;

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

Reference yield:

(1S,2R,6S,7R)-4-Benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]decane-10-carbaldehyde (214558-26-6) → (1S,2S,6R,7R,10R)-10-Allyl-4-benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]decane-10-carbaldehyde (214406-67-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / KH / tetrahydrofuran

2: 75 percent / xylene / 96 h / Heating

With potassium hydride; In tetrahydrofuran; xylene;

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,2S,6R,7R,10R)-10-Allyl-4-benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]decane-10-carbaldehyde (214406-67-4)

Guidance literature:

Multi-step reaction with 5 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

4: 41 percent / KH / tetrahydrofuran

5: 75 percent / xylene / 96 h / Heating

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

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

upstream raw materials:

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

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

Downstream raw materials:

(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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