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

Base Information

Chemical Name:4-[(1SR)-benzyloxycarbonylamino-(4R)-carboxy-2-iodopent-(2Z)-enyl]benzoic acid methyl ester
CAS No.:935431-08-6
Molecular Formula:C₂₂H₂₂INO₆
Molecular Weight:523.324
Hs Code.:

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

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

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

There total 4 articles about 4-[(1SR)-benzyloxycarbonylamino-(4R)-carboxy-2-iodopent-(2Z)-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: 95.0%

: 935430-83-4
4-[(1SR)-benzyloxycarbonylamino-2-iodo-(4R)-methyl-5-oxopent-(2Z)-enyl]benzoic acid methyl ester

: 935431-08-6
4-[(1SR)-benzyloxycarbonylamino-(4R)-carboxy-2-iodopent-(2Z)-enyl]benzoic acid methyl ester

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1002/adsc.200505171

Reference yield:

: 914652-74-7
4-[(1SR)-benzyloxycarbonylamino-5-hydroxy-2-iodo-(4R)-methylpent-(2Z)-enyl]benzoic acid methyl ester

: 935431-08-6
4-[(1SR)-benzyloxycarbonylamino-(4R)-carboxy-2-iodopent-(2Z)-enyl]benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

1.2: 92 percent / aq. Na₂S₂O₃; aq. NaHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

2.1: 95 percent / 2-methyl-2-butene; aq. NaClO₂; aq. NaH₂PO₄*H₂O / tetrahydrofuran / 0 - 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 1.1: Dess-Martin oxidation;
DOI:10.1002/adsc.200505171

Reference yield:

: 914652-59-8
N-[5-(tert-butyldiphenylsilanyloxy)-2-iodo-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2Z)-enyl]-P,P-diphenylphosphinamide

: 935431-08-6
4-[(1SR)-benzyloxycarbonylamino-(4R)-carboxy-2-iodopent-(2Z)-enyl]benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: HCl / methanol / 0 °C

1.2: NaHCO₃ / ethyl acetate; H₂O / 0.25 h

1.3: 70 percent / ethyl acetate; H₂O / 2 h / 0 °C

2.1: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

2.2: 92 percent / aq. Na₂S₂O₃; aq. NaHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 95 percent / 2-methyl-2-butene; aq. NaClO₂; aq. NaH₂PO₄*H₂O / tetrahydrofuran / 0 - 20 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; 2.1: Dess-Martin oxidation;
DOI:10.1002/adsc.200505171