2-{3-[(allyl-tert-butoxycarbonyl-amino)-methyl]-furan-2-yl}-4-benzyloxy-6-hydroxy-benzoic acid but-3-enyl ester

Base Information

• Chemical Name: 2-{3-[(allyl-tert-butoxycarbonyl-amino)-methyl]-furan-2-yl}-4-benzyloxy-6-hydroxy-benzoic acid but-3-enyl ester
• CAS No.: 884864-66-8
• Molecular Formula: C₃₁H₃₅NO₇
• Molecular Weight: 533.621

Synonyms:2-{3-[(allyl-tert-butoxycarbonyl-amino)-methyl]-furan-2-yl}-4-benzyloxy-6-hydroxy-benzoic acid but-3-enyl ester

Chemical Property of 2-{3-[(allyl-tert-butoxycarbonyl-amino)-methyl]-furan-2-yl}-4-benzyloxy-6-hydroxy-benzoic acid but-3-enyl ester

Chemical Property:

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Technology Process of 2-{3-[(allyl-tert-butoxycarbonyl-amino)-methyl]-furan-2-yl}-4-benzyloxy-6-hydroxy-benzoic acid but-3-enyl ester

There total 8 articles about 2-{3-[(allyl-tert-butoxycarbonyl-amino)-methyl]-furan-2-yl}-4-benzyloxy-6-hydroxy-benzoic acid but-3-enyl 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:

acide 2,4,6-trihydroxybenzoique (83-30-7) → 2-{3-[(allyl-tert-butoxycarbonyl-amino)-methyl]-furan-2-yl}-4-benzyloxy-6-hydroxy-benzoic acid but-3-enyl ester (884864-66-8)

Guidance literature:

Multi-step reaction with 8 steps

1: trifluoroacetic acid; trifluoroacetic anhydride

2: pyridine / CH₂Cl₂

3: Pd(Ph₃P)2Cl₂ / dimethylformamide / 1 h / 60 °C

4: NaBH(OAc)3; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

5: CH₂Cl₂ / 3 h

6: KOH / dimethylsulfoxide / 1 h / 65 °C

With pyridine; potassium hydroxide; 4 A molecular sieve; sodium tris(acetoxy)borohydride; trifluoroacetic acid; trifluoroacetic anhydride; bis-triphenylphosphine-palladium(II) chloride; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 2: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2006.01.117

Reference yield:

5,7-dihydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (137571-73-4) → 2-{3-[(allyl-tert-butoxycarbonyl-amino)-methyl]-furan-2-yl}-4-benzyloxy-6-hydroxy-benzoic acid but-3-enyl ester (884864-66-8)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / CH₂Cl₂

2: Pd(Ph₃P)2Cl₂ / dimethylformamide / 1 h / 60 °C

3: NaBH(OAc)3; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

4: CH₂Cl₂ / 3 h

5: KOH / dimethylsulfoxide / 1 h / 65 °C

With pyridine; potassium hydroxide; 4 A molecular sieve; sodium tris(acetoxy)borohydride; bis-triphenylphosphine-palladium(II) chloride; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2006.01.117

Reference yield:

7-(benzyloxy)-2,2-dimethyl-5-<(trifluoromethyl)sulfonyl>-4H-1,3-benzodioxin-4-one (137571-75-6) → 2-{3-[(allyl-tert-butoxycarbonyl-amino)-methyl]-furan-2-yl}-4-benzyloxy-6-hydroxy-benzoic acid but-3-enyl ester (884864-66-8)

Guidance literature:

Multi-step reaction with 5 steps

1: Pd(Ph₃P)2Cl₂ / dimethylformamide / 1 h / 60 °C

2: NaBH(OAc)3; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

3: CH₂Cl₂ / 3 h

4: KOH / dimethylsulfoxide / 1 h / 65 °C

With potassium hydroxide; 4 A molecular sieve; sodium tris(acetoxy)borohydride; bis-triphenylphosphine-palladium(II) chloride; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2006.01.117

upstream raw materials:

homoalylic alcohol

acide 2,4,6-trihydroxybenzoique

5,7-dihydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

7-(benzyloxy)-5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

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