(2R,5R)-2-((1S,2R)-2-Benzyloxycarbonylamino-1,3-dihydroxy-propyl)-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester

Base Information

Chemical Name:(2R,5R)-2-((1S,2R)-2-Benzyloxycarbonylamino-1,3-dihydroxy-propyl)-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester
CAS No.:433237-95-7
Molecular Formula:C₅₅H₅₃Cl₂N₃O₁₂
Molecular Weight:1018.94
Hs Code.:

(2R,5R)-2-((1S,2R)-2-Benzyloxycarbonylamino-1,3-dihydroxy-propyl)-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester

Synonyms:(2R,5R)-2-((1S,2R)-2-Benzyloxycarbonylamino-1,3-dihydroxy-propyl)-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester

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Chemical Property of (2R,5R)-2-((1S,2R)-2-Benzyloxycarbonylamino-1,3-dihydroxy-propyl)-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester

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Technology Process of (2R,5R)-2-((1S,2R)-2-Benzyloxycarbonylamino-1,3-dihydroxy-propyl)-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester

There total 13 articles about (2R,5R)-2-((1S,2R)-2-Benzyloxycarbonylamino-1,3-dihydroxy-propyl)-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid dibenzyl 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: 50.0%

: (2R,5R)-2-[(1S,2R)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester

: 433237-95-7
(2R,5R)-2-((1S,2R)-2-Benzyloxycarbonylamino-1,3-dihydroxy-propyl)-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/S0040-4039(01)02254-7

Reference yield:

: 81286-82-0
(2R,5S)-2-tert-butyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one

: 433237-95-7
(2R,5R)-2-((1S,2R)-2-Benzyloxycarbonylamino-1,3-dihydroxy-propyl)-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: LDA / tetrahydrofuran / -78 °C

2: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 °C

3: 48 percent / NaBH₄ / methanol; tetrahydrofuran / 0 °C

4: aq. H₂SO₄ / dioxane / 20 - 80 °C

5: NaHCO₃ / tetrahydrofuran; dimethylformamide / 20 °C

6: Et₃N; DMAP / CH₂Cl₂ / 20 °C

7: 62 percent / aq. AcOH / 60 °C

8: 80 percent / imidazole / dimethylformamide / 0 °C

9: 85 percent / MeReO₃; urea*H₂O₂ / methanol / 20 °C

10: 85 percent / Zn; CuI / tetrahydrofuran; H₂O / 20 °C / ultrasound

11: 71 percent / Zn; NH₄Cl / ethanol / 90 °C

12: K₂CO₃ / toluene; H₂O

13: 50 percent / TBAF; AcOH / tetrahydrofuran / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; copper(l) iodide; sulfuric acid; tetrabutyl ammonium fluoride; urea hydrogen peroxide adduct; methyltrioxorhenium(VII); sodium hydrogencarbonate; potassium carbonate; ammonium chloride; Dess-Martin periodane; acetic acid; triethylamine; zinc; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(01)02254-7

Reference yield:

: 100-39-0
benzyl bromide

: 433237-95-7
(2R,5R)-2-((1S,2R)-2-Benzyloxycarbonylamino-1,3-dihydroxy-propyl)-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: NaHCO₃ / tetrahydrofuran; dimethylformamide / 20 °C

2: Et₃N; DMAP / CH₂Cl₂ / 20 °C

3: 62 percent / aq. AcOH / 60 °C

4: 80 percent / imidazole / dimethylformamide / 0 °C

5: 85 percent / MeReO₃; urea*H₂O₂ / methanol / 20 °C

6: 85 percent / Zn; CuI / tetrahydrofuran; H₂O / 20 °C / ultrasound

7: 71 percent / Zn; NH₄Cl / ethanol / 90 °C

8: K₂CO₃ / toluene; H₂O

9: 50 percent / TBAF; AcOH / tetrahydrofuran / 20 °C

With 1H-imidazole; dmap; copper(l) iodide; tetrabutyl ammonium fluoride; urea hydrogen peroxide adduct; methyltrioxorhenium(VII); sodium hydrogencarbonate; potassium carbonate; ammonium chloride; acetic acid; triethylamine; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(01)02254-7