benzyl (1R,2'R,E)-2-{2'-[(tert-butoxy)carbonylamino]-3'-iodopropylidene}cyclopentanecarboxylate

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Chemical Name:benzyl (1R,2'R,E)-2-{2'-[(tert-butoxy)carbonylamino]-3'-iodopropylidene}cyclopentanecarboxylate
CAS No.:462653-02-7
Molecular Formula:C₂₁H₂₈INO₄
Molecular Weight:485.362
Hs Code.:

Synonyms:benzyl (1R,2'R,E)-2-{2'-[(tert-butoxy)carbonylamino]-3'-iodopropylidene}cyclopentanecarboxylate

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Chemical Property of benzyl (1R,2'R,E)-2-{2'-[(tert-butoxy)carbonylamino]-3'-iodopropylidene}cyclopentanecarboxylate

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Technology Process of benzyl (1R,2'R,E)-2-{2'-[(tert-butoxy)carbonylamino]-3'-iodopropylidene}cyclopentanecarboxylate

There total 11 articles about benzyl (1R,2'R,E)-2-{2'-[(tert-butoxy)carbonylamino]-3'-iodopropylidene}cyclopentanecarboxylate 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: 67.0%

: 462653-01-6
(R)-2-[(R)-2-tert-Butoxycarbonylamino-3-(toluene-4-sulfonyloxy)-prop-(E)-ylidene]-cyclopentanecarboxylic acid benzyl ester

: 462653-02-7
benzyl (1R,2'R,E)-2-{2'-[(tert-butoxy)carbonylamino]-3'-iodopropylidene}cyclopentanecarboxylate

Guidance literature:: With sodium iodide; In acetone; at 20 ℃; for 30h;
DOI:10.1021/jo025922u

Reference yield:

: 17497-52-8
1-iodocyclopentene

: 462653-02-7
benzyl (1R,2'R,E)-2-{2'-[(tert-butoxy)carbonylamino]-3'-iodopropylidene}cyclopentanecarboxylate

Guidance literature:: Multi-step reaction with 11 steps

1.1: diisobutylaluminum hydride / CH₂Cl₂; toluene / 1 h / -78 °C

1.2: 6.3 g / BuLi; ZnCl₂; LiCl / tetrahydrofuran; hexane; CH₂Cl₂ / -78 - 20 °C

2.1: NaH / tetrahydrofuran / 0.5 h / Heating

2.2: 884 mg / tetrahydrofuran / 3 h / 20 °C

3.1: 98 percent / CuCN; LiCl / tetrahydrofuran / 3.5 h / -78 - 0 °C

4.1: 79 percent / KF; H₂O₂ / dimethylformamide; H₂O / 10 h / 20 °C

5.1: Dess-Martin periodinane / CHCl₃ / 1 h / 20 °C

6.1: 248 mg / NaClO₂; 2-methyl-2-butene; Na₂HPO₄ / 2-methyl-propan-2-ol; H₂O / 15 h / 20 °C

7.1: 70 percent / dicyclohexylamine / dimethylformamide / 20 °C

8.1: CF₃COOH / CH₂Cl₂ / 1 h / 0 °C

9.1: 152 mg / Et₃N / tetrahydrofuran / 20 °C

10.1: 71 percent / pyridine / CHCl₃ / 0.5 h / 0 °C

11.1: 67 percent / NaI / acetone / 30 h / 20 °C

With pyridine; potassium fluoride; sodium chlorite; disodium hydrogenphosphate; 2-methyl-but-2-ene; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; N-cyclohexyl-cyclohexanamine; trifluoroacetic acid; sodium iodide; lithium chloride; In tetrahydrofuran; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
DOI:10.1021/jo025922u

Reference yield:

: 462652-94-4
(1S,2S)-(tert-butoxy)-N-{1-[(tert-butoxy)methyl]-2-cyclopent-1-en-1-yl-2-hydroxyethyl}carboxamide

: 462653-02-7
benzyl (1R,2'R,E)-2-{2'-[(tert-butoxy)carbonylamino]-3'-iodopropylidene}cyclopentanecarboxylate

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH / tetrahydrofuran / 0.5 h / Heating

1.2: 884 mg / tetrahydrofuran / 3 h / 20 °C

2.1: 98 percent / CuCN; LiCl / tetrahydrofuran / 3.5 h / -78 - 0 °C

3.1: 79 percent / KF; H₂O₂ / dimethylformamide; H₂O / 10 h / 20 °C

4.1: Dess-Martin periodinane / CHCl₃ / 1 h / 20 °C

5.1: 248 mg / NaClO₂; 2-methyl-2-butene; Na₂HPO₄ / 2-methyl-propan-2-ol; H₂O / 15 h / 20 °C

6.1: 70 percent / dicyclohexylamine / dimethylformamide / 20 °C

7.1: CF₃COOH / CH₂Cl₂ / 1 h / 0 °C

8.1: 152 mg / Et₃N / tetrahydrofuran / 20 °C

9.1: 71 percent / pyridine / CHCl₃ / 0.5 h / 0 °C

10.1: 67 percent / NaI / acetone / 30 h / 20 °C

With pyridine; potassium fluoride; sodium chlorite; disodium hydrogenphosphate; 2-methyl-but-2-ene; dihydrogen peroxide; sodium hydride; Dess-Martin periodane; triethylamine; N-cyclohexyl-cyclohexanamine; trifluoroacetic acid; sodium iodide; lithium chloride; In tetrahydrofuran; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1021/jo025922u