2-[4-(2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-phenyl]-malonic acid di-tert-butyl ester

Base Information

• Chemical Name: 2-[4-(2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-phenyl]-malonic acid di-tert-butyl ester
• CAS No.: 853063-41-9
• Molecular Formula: C₂₉H₃₅NO₈
• Molecular Weight: 525.599

Synonyms:2-[4-(2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-phenyl]-malonic acid di-tert-butyl ester

Chemical Property of 2-[4-(2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-phenyl]-malonic acid di-tert-butyl ester

Chemical Property:

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Technology Process of 2-[4-(2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-phenyl]-malonic acid di-tert-butyl ester

There total 4 articles about 2-[4-(2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-phenyl]-malonic acid di-tert-butyl 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: 79.0%

methyl 2-(N-Cbz-amino)-2-dimethylphosphonylacetate + di-tert-butyl 2-(4-formylphenyl)malonate (853063-38-4) → 2-[4-(2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-phenyl]-malonic acid di-tert-butyl ester (853063-41-9)

Guidance literature:

With 1,1,3,3-tetramethylguanidine; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/j.tetlet.2005.03.105

Reference yield:

2-(4-diethoxymethyl-phenyl)-malonic acid di-tert-butyl ester → 2-[4-(2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-phenyl]-malonic acid di-tert-butyl ester (853063-41-9)

Guidance literature:

Multi-step reaction with 2 steps

1: citric acid; water

2: 79 percent / tetramethylguanidine / tetrahydrofuran / -78 - 20 °C

With 1,1,3,3-tetramethylguanidine; water; citric acid; In tetrahydrofuran; 2: Horner-Emmons olefination;

DOI:10.1016/j.tetlet.2005.03.105

Reference yield:

t-butyl malonate (541-16-2) → 2-[4-(2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-phenyl]-malonic acid di-tert-butyl ester (853063-41-9)

Guidance literature:

Multi-step reaction with 3 steps

1: P(tBu)3; KOtBu; Pd(dba)2 / dioxane / 6 h / 80 °C

2: citric acid; water

3: 79 percent / tetramethylguanidine / tetrahydrofuran / -78 - 20 °C

With tri-tert-butyl phosphine; 1,1,3,3-tetramethylguanidine; potassium tert-butylate; water; citric acid; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; 3: Horner-Emmons olefination;

DOI:10.1016/j.tetlet.2005.03.105

upstream raw materials:

di-tert-butyl 2-(4-formylphenyl)malonate

t-butyl malonate

4-bromobenzaldehyde diethyl acetal

Downstream raw materials:

N^α-Fmoc-4-(di-tert-butoxycarbonyl-methyl)-L-phenylalanine

4-(Bis((tert-butyl)oxycarbonyl)methyl)-L-phenylalanine

2-[4-(2-benzyloxycarbonylamino-2-carboxy-ethyl)-phenyl]-malonic acid di-tert-butyl ester

2-[4-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-phenyl]-malonic acid di-tert-butyl ester

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