(2R,5R)-2-((1S,2S)-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,2S)-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.: 420107-69-3
• Molecular Formula: C₅₅H₅₃Cl₂N₃O₁₂
• Molecular Weight: 1018.94
• Mol file: 420107-69-3.mol

Synonyms:(2R,5R)-2-((1S,2S)-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

Chemical Property of (2R,5R)-2-((1S,2S)-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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5R)-2-((1S,2S)-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 18 articles about (2R,5R)-2-((1S,2S)-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:

(3R,7aS)-3-tert-Butyl-tetrahydro-pyrrolo[1,2-c]oxazol-1-one (81286-82-0,119816-46-5) → (2R,5R)-2-((1S,2S)-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 (420107-69-3)

Guidance literature:

Multi-step reaction with 13 steps

1: LDA / tetrahydrofuran / -78 °C

2: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0 °C

3: NaBH₄ / ethanol; tetrahydrofuran / 0 °C

4: aq. H₂SO₄; 1,4-dioxane / 20 - 80 °C

5: DBU / acetonitrile / 20 °C

6: Et₃N; DMAP / CH₂Cl₂ / 20 °C

7: 52 percent / aq. AcOH / 60 °C

8: 96 percent / imidazol / dimethylformamide / 0 °C

9: 84 percent / MeReO₃; urea*H₂O₂ / methanol / 20 °C

10: 75 percent / Zn; CuI / tetrahydrofuran; H₂O / 20 °C / ultrasound irradiation

11: 98 percent / Zn; satd. NH₄Cl / ethanol / 90 °C

12: K₂CO₃ / toluene; H₂O

13: methanol / 20 °C

With 1,4-dioxane; pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; copper(l) iodide; sulfuric acid; urea hydrogen peroxide adduct; methyltrioxorhenium(VII); potassium carbonate; ammonium chloride; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4039(01)02255-9

Reference yield:

benzyl bromide (100-39-0) → (2R,5R)-2-((1S,2S)-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 (420107-69-3)

Guidance literature:

Multi-step reaction with 9 steps

1: DBU / acetonitrile / 20 °C

2: Et₃N; DMAP / CH₂Cl₂ / 20 °C

3: 52 percent / aq. AcOH / 60 °C

4: 96 percent / imidazol / dimethylformamide / 0 °C

5: 84 percent / MeReO₃; urea*H₂O₂ / methanol / 20 °C

6: 75 percent / Zn; CuI / tetrahydrofuran; H₂O / 20 °C / ultrasound irradiation

7: 98 percent / Zn; satd. NH₄Cl / ethanol / 90 °C

8: K₂CO₃ / toluene; H₂O

9: methanol / 20 °C

With 1H-imidazole; dmap; copper(l) iodide; urea hydrogen peroxide adduct; methyltrioxorhenium(VII); potassium carbonate; ammonium chloride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4039(01)02255-9

Reference yield:

L-serine benzyl ester hydrochloride (60022-62-0,879278-55-4,151651-44-4) → (2R,5R)-2-((1S,2S)-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 (420107-69-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / BOP; triethylamine / CH₂Cl₂ / 0 - 20 °C

2: 74 percent / Et₃N / CH₂Cl₂ / 0 °C

3: 84 percent / NaI / acetone / 20 °C

4: 75 percent / Zn; CuI / tetrahydrofuran; H₂O / 20 °C / ultrasound irradiation

5: 98 percent / Zn; satd. NH₄Cl / ethanol / 90 °C

6: K₂CO₃ / toluene; H₂O

7: methanol / 20 °C

With copper(l) iodide; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; ammonium chloride; triethylamine; sodium iodide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; toluene;

DOI:10.1016/S0040-4039(01)02255-9

upstream raw materials:

chloro-trimethyl-silane

benzyl bromide

L-serine benzyl ester hydrochloride

(3R,7aS)-3-tert-Butyl-tetrahydro-pyrrolo[1,2-c]oxazol-1-one

Downstream raw materials:

(-)-Kaitocephalin

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