(1R,7R,8R)-7-(tert-butyldiphenylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)pyrrolizidine

Base Information

Chemical Name:(1R,7R,8R)-7-(tert-butyldiphenylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)pyrrolizidine
CAS No.:328404-70-2
Molecular Formula:C₄₀H₅₁NO₂Si₂
Molecular Weight:634.021
Hs Code.:

Synonyms:(1R,7R,8R)-7-(tert-butyldiphenylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)pyrrolizidine

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Chemical Property of (1R,7R,8R)-7-(tert-butyldiphenylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)pyrrolizidine

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Technology Process of (1R,7R,8R)-7-(tert-butyldiphenylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)pyrrolizidine

There total 10 articles about (1R,7R,8R)-7-(tert-butyldiphenylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)pyrrolizidine 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: 92.0%

: 328404-69-9
3-(tert-butyl-diphenyl-silanyloxy)-2-[1-(tert-butyl-diphenyl-silanyloxymethyl)-3-methanesulfonyloxy-propyl]-pyrrolidine-1-carboxylic acid benzyl ester

: 328404-70-2
(1R,7R,8R)-7-(tert-butyldiphenylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)pyrrolizidine

Guidance literature:: With hydrogen; cyclohexene; palladium on activated charcoal; In methanol; Heating;
DOI:10.1016/S0040-4039(00)01664-6

Reference yield:

: 95456-65-8
(1R,5R)-(-)-6-aza-6-benzyloxycarbonyl-2-oxabicyclo[3.3.0]octan-3-one

: 328404-70-2
(1R,7R,8R)-7-(tert-butyldiphenylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)pyrrolizidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

1.2: 57 percent / hexamethylphosphoric acid triamide; tetrahydrofuran / 1.5 h / -78 - -45 °C

2.1: 86 percent / NaBH₄ / aq. ethanol / 22 h / 20 °C

3.1: imidazole / dimethylformamide / 20 h / 20 °C

3.2: OsO₄; NaIO₄ / diethyl ether; H₂O / 36 h / 20 °C

3.3: 238.4 mg / NaBH₄ / aq. ethanol / 2 h / 0 °C

4.1: 88 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5.1: 88 percent / cyclohexene / Pd/C / methanol / 1.25 h / 0 °C / Heating

6.1: 86 mg / K₂CO₃ / methanol / 1 h / Heating

With 1H-imidazole; sodium tetrahydroborate; potassium carbonate; triethylamine; lithium hexamethyldisilazane; cyclohexene; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; N,N-dimethyl-formamide; 3.2: Lemieux-Johnson oxidation;
DOI:10.1021/jo010753j

Reference yield:

: 328404-56-4
(R)-3-[(1-bezyloxy-carbonyl)-pyrrolidinyl]-α-diazoacetate

: 328404-70-2
(1R,7R,8R)-7-(tert-butyldiphenylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)pyrrolizidine

Guidance literature:: Multi-step reaction with 7 steps

1.1: 78 percent / Rh₂[(4R)-1-(3-(PhCH₂CH₂CO)-2-imidazolidinone-4-COOMe)] / 1,2-dichloro-ethane / 2 h / 60 °C

2.1: LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

2.2: 57 percent / hexamethylphosphoric acid triamide; tetrahydrofuran / 1.5 h / -78 - -45 °C

3.1: 86 percent / NaBH₄ / aq. ethanol / 22 h / 20 °C

4.1: imidazole / dimethylformamide / 20 h / 20 °C

4.2: OsO₄; NaIO₄ / diethyl ether; H₂O / 36 h / 20 °C

4.3: 238.4 mg / NaBH₄ / aq. ethanol / 2 h / 0 °C

5.1: 88 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 88 percent / cyclohexene / Pd/C / methanol / 1.25 h / 0 °C / Heating

7.1: 86 mg / K₂CO₃ / methanol / 1 h / Heating

With 1H-imidazole; sodium tetrahydroborate; potassium carbonate; triethylamine; lithium hexamethyldisilazane; cyclohexene; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 4.2: Lemieux-Johnson oxidation;
DOI:10.1021/jo010753j