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

Base Information

Chemical Name:4-[(1SR)-benzyloxycarbonylamino-5-hydroxy-(4R)-methyl-2-phenylpent-(2E)-enyl]benzoic acid methyl ester
CAS No.:914652-71-4
Molecular Formula:C₂₈H₂₉NO₅
Molecular Weight:459.542
Hs Code.:

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

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

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

There total 4 articles about 4-[(1SR)-benzyloxycarbonylamino-5-hydroxy-(4R)-methyl-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: 79.0%

: 914652-61-2
N-[5-(tert-butyldiphenylsilanyloxy)-2-phenyl-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2E)-enyl]-P,P-diphenylphosphinamide

: 501-53-1,94274-21-2
benzyl chloroformate

: 914652-71-4
4-[(1SR)-benzyloxycarbonylamino-5-hydroxy-(4R)-methyl-2-phenylpent-(2E)-enyl]benzoic acid methyl ester

Guidance literature:: N-[5-(tert-butyldiphenylsilanyloxy)-2-phenyl-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2E)-enyl]-P,P-diphenylphosphinamide; With hydrogenchloride; In methanol; at 20 ℃;

With sodium hydrogencarbonate; In water; ethyl acetate; for 0.25h;

benzyl chloroformate; In water; ethyl acetate; at 0 ℃; for 2h;
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

: 914652-71-4
4-[(1SR)-benzyloxycarbonylamino-5-hydroxy-(4R)-methyl-2-phenylpent-(2E)-enyl]benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 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

With hydrogenchloride; N-iodo-succinimide; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2.2: Negishi coupling;
DOI:10.1002/adsc.200505171

Reference yield:

: 591-50-4
iodobenzene

: 914652-71-4
4-[(1SR)-benzyloxycarbonylamino-5-hydroxy-(4R)-methyl-2-phenylpent-(2E)-enyl]benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 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

With hydrogenchloride; copper(l) chloride; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; dimethyl sulfoxide; 1.1: Stille coupling;
DOI:10.1002/adsc.200505171