4-[(1SR)-benzyloxycarbonylamino-(4R)-carboxy-2-phenylpent-(2E)-enyl]benzoic acid methyl ester

Base Information

• Chemical Name: 4-[(1SR)-benzyloxycarbonylamino-(4R)-carboxy-2-phenylpent-(2E)-enyl]benzoic acid methyl ester
• CAS No.: 935428-41-4
• Molecular Formula: C₂₈H₂₇NO₆
• Molecular Weight: 473.525

Synonyms:4-[(1SR)-benzyloxycarbonylamino-(4R)-carboxy-2-phenylpent-(2E)-enyl]benzoic acid methyl ester

Chemical Property of 4-[(1SR)-benzyloxycarbonylamino-(4R)-carboxy-2-phenylpent-(2E)-enyl]benzoic acid methyl ester

Chemical Property:

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Technology Process of 4-[(1SR)-benzyloxycarbonylamino-(4R)-carboxy-2-phenylpent-(2E)-enyl]benzoic acid methyl ester

There total 6 articles about 4-[(1SR)-benzyloxycarbonylamino-(4R)-carboxy-2-phenylpent-(2E)-enyl]benzoic acid methyl 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: 90.0%

4-[(1SR)-benzyloxycarbonylamino-(4R)-methyl-5-oxo-2-phenylpent-(2E)-enyl]benzoic acid methyl ester → 4-[(1SR)-benzyloxycarbonylamino-(4R)-carboxy-2-phenylpent-(2E)-enyl]benzoic acid methyl ester (935428-41-4)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; at 0 ℃; for 4h;

DOI:10.1002/adsc.200505171

Reference yield:

N-[5-(tert-butyldiphenylsilanyloxy)-2-tributyltinyl-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2Z)-enyl]-P,P-diphenylphosphinamide → 4-[(1SR)-benzyloxycarbonylamino-(4R)-carboxy-2-phenylpent-(2E)-enyl]benzoic acid methyl ester (935428-41-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 63 percent / NIS / CH₂Cl₂ / 0.07 h / 20 °C

2.1: ZnCl₂ / tetrahydrofuran; diethyl ether / 0 - 20 °C

2.2: 86 percent / Pd(PPh₃)4 / tetrahydrofuran; diethyl ether / 4 h / 55 - 60 °C

3.1: HCl / methanol / 20 °C

3.2: NaHCO₃ / ethyl acetate; H₂O / 0.25 h

3.3: 79 percent / ethyl acetate; H₂O / 2 h / 0 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 0 °C

4.2: 87 percent / aq. Na₂S₂O₃; aq. NaHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

5.1: 90 percent / 2-methyl-2-butene; aq. NaClO₂; aq. NaH₂PO₄*H₂O / tetrahydrofuran / 4 h / 0 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; N-iodo-succinimide; 2-methyl-but-2-ene; Dess-Martin periodane; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2.2: Negishi coupling / 4.1: Dess-Martin oxidation;

DOI:10.1002/adsc.200505171

Reference yield:

iodobenzene (591-50-4) → 4-[(1SR)-benzyloxycarbonylamino-(4R)-carboxy-2-phenylpent-(2E)-enyl]benzoic acid methyl ester (935428-41-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 63 percent / LiCl; CuCl / Pd(PPh₃)4 / dimethylsulfoxide / 0.67 h / 60 °C / microwave irradiation

2.1: HCl / methanol / 20 °C

2.2: NaHCO₃ / ethyl acetate; H₂O / 0.25 h

2.3: 79 percent / ethyl acetate; H₂O / 2 h / 0 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 0 °C

3.2: 87 percent / aq. Na₂S₂O₃; aq. NaHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 90 percent / 2-methyl-2-butene; aq. NaClO₂; aq. NaH₂PO₄*H₂O / tetrahydrofuran / 4 h / 0 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; Dess-Martin periodane; copper(l) chloride; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 1.1: Stille coupling / 3.1: Dess-Martin oxidation;

DOI:10.1002/adsc.200505171

upstream raw materials:

4-[(1SR)-benzyloxycarbonylamino-5-hydroxy-(4R)-methyl-2-phenylpent-(2E)-enyl]benzoic acid methyl ester

N-[5-(tert-butyldiphenylsilanyloxy)-2-iodo-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2Z)-enyl]-P,P-diphenylphosphinamide

N-[5-(tert-butyldiphenylsilanyloxy)-2-phenyl-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2E)-enyl]-P,P-diphenylphosphinamide

iodobenzene

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