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

Base Information

• Chemical Name: (2R,5R)-2-[(1S,2S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-2-carboxylic acid benzyl ester
• CAS No.: 420107-74-0
• Molecular Formula: C₆₆H₇₃Cl₂N₃O₁₀Si₂
• Molecular Weight: 1195.4
• Mol file: 420107-74-0.mol

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

Chemical Property of (2R,5R)-2-[(1S,2S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5R)-2-[(1S,2S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-2-carboxylic acid benzyl ester

There total 16 articles about (2R,5R)-2-[(1S,2S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-2-carboxylic acid benzyl 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: 98.0%

(2R,5R)-2-[(1S,2S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-1-hydroxy-pyrrolidine-2-carboxylic acid benzyl ester (420107-68-2) → (2R,5R)-2-[(1S,2S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-2-carboxylic acid benzyl ester (420107-74-0)

Guidance literature:

With ammonium chloride; zinc; In ethanol; at 90 ℃;

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

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-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-2-carboxylic acid benzyl ester (420107-74-0)

Guidance literature:

Multi-step reaction with 11 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

With 1,4-dioxane; pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; copper(l) iodide; sulfuric acid; urea hydrogen peroxide adduct; methyltrioxorhenium(VII); 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; acetonitrile;

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

Reference yield:

benzyl bromide (100-39-0) → (2R,5R)-2-[(1S,2S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-2-carboxylic acid benzyl ester (420107-74-0)

Guidance literature:

Multi-step reaction with 7 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

With 1H-imidazole; dmap; copper(l) iodide; urea hydrogen peroxide adduct; methyltrioxorhenium(VII); 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; acetonitrile;

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

upstream raw materials:

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

benzyl bromide

L-serine benzyl ester hydrochloride

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

Downstream raw materials:

(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

(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

(-)-Kaitocephalin