(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

Base Information

• Chemical Name: (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
• CAS No.: 214406-64-1
• Molecular Formula: C₂₁H₂₃NO₅
• Molecular Weight: 369.417

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 7 articles about (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 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: 68.0%

(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) → (1R,2R,6S,7S,10R)-10-Allyl-4-benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]decane-10-carboxylic acid (214406-64-1)

Guidance literature:

With sodium chlorite; camphor-10-sulfonic acid; In water; tert-butyl alcohol;

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) → (1R,2R,6S,7S,10R)-10-Allyl-4-benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]decane-10-carboxylic acid (214406-64-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 41 percent / KH / tetrahydrofuran

2: 75 percent / xylene / 96 h / Heating

3: 68 percent / NaClO₂, aq. NaHPO₄ / 2-methyl-propan-2-ol; H₂O

With sodium chlorite; camphor-10-sulfonic acid; potassium hydride; In tetrahydrofuran; water; xylene; tert-butyl alcohol;

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) → (1R,2R,6S,7S,10R)-10-Allyl-4-benzyloxymethyl-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]decane-10-carboxylic acid (214406-64-1)

Guidance literature:

Multi-step reaction with 6 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

6: 68 percent / NaClO₂, aq. NaHPO₄ / 2-methyl-propan-2-ol; H₂O

With triethylsilane; sodium chlorite; n-butyllithium; camphor-10-sulfonic acid; potassium hydride; trifluoroacetic acid; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; dichloromethane; water; acetonitrile; xylene; tert-butyl alcohol;

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

upstream 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

(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 naphthalen-2-yl ester

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