(R)-2-[(1S,2R)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-pyrrolidine-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (R)-2-[(1S,2R)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-pyrrolidine-2-carboxylic acid benzyl ester
• CAS No.: 844693-11-4
• Molecular Formula: C₄₂H₅₄N₂O₆Si₂
• Molecular Weight: 739.072

Synonyms:(R)-2-[(1S,2R)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-pyrrolidine-2-carboxylic acid benzyl ester

Chemical Property of (R)-2-[(1S,2R)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-pyrrolidine-2-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (R)-2-[(1S,2R)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-pyrrolidine-2-carboxylic acid benzyl ester

There total 9 articles about (R)-2-[(1S,2R)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-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: 80.0%

chloro-trimethyl-silane (75-77-4) + (R)-2-[(1S,2R)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-propyl]-pyrrolidine-2-carboxylic acid benzyl ester → (R)-2-[(1S,2R)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-pyrrolidine-2-carboxylic acid benzyl ester (844693-11-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1016/S0040-4039(01)02254-7

Reference yield:

(2R,5S)-2-tert-butyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one (81286-82-0) → (R)-2-[(1S,2R)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-pyrrolidine-2-carboxylic acid benzyl ester (844693-11-4)

Guidance literature:

Multi-step reaction with 8 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

With 1H-imidazole; dmap; sodium tetrahydroborate; sulfuric acid; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)02254-7

Reference yield:

benzyl bromide (100-39-0) → (R)-2-[(1S,2R)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-pyrrolidine-2-carboxylic acid benzyl ester (844693-11-4)

Guidance literature:

Multi-step reaction with 4 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

With 1H-imidazole; dmap; sodium hydrogencarbonate; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)02254-7

upstream raw materials:

chloro-trimethyl-silane

benzyl bromide

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

4-(3-tert-butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carbonyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Downstream raw materials:

kaitocephalin

(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

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

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