benzyl N-acetyl-{4-[3,5-bis(tert-butyldimethylsilyloxy)-2-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentyl]butylamino}acetate

Base Information

Chemical Name:benzyl N-acetyl-{4-[3,5-bis(tert-butyldimethylsilyloxy)-2-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentyl]butylamino}acetate
CAS No.:333968-48-2
Molecular Formula:C₄₈H₈₃NO₇Si₃
Molecular Weight:870.446
Hs Code.:

Synonyms:benzyl N-acetyl-{4-[3,5-bis(tert-butyldimethylsilyloxy)-2-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentyl]butylamino}acetate

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Chemical Property of benzyl N-acetyl-{4-[3,5-bis(tert-butyldimethylsilyloxy)-2-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentyl]butylamino}acetate

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Technology Process of benzyl N-acetyl-{4-[3,5-bis(tert-butyldimethylsilyloxy)-2-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentyl]butylamino}acetate

There total 12 articles about benzyl N-acetyl-{4-[3,5-bis(tert-butyldimethylsilyloxy)-2-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentyl]butylamino}acetate 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: 99.0%

: 108-24-7
acetic anhydride

: 333968-44-8
benzyl {4-[3,5-bis(tert-butyldimethylsilyloxy)-2-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentyl]butylamino}acetate

: 333968-48-2
benzyl N-acetyl-{4-[3,5-bis(tert-butyldimethylsilyloxy)-2-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentyl]butylamino}acetate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ol015613a

Reference yield:

: (2R,3R,4R)-2-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-butyl]-cyclopentanol

: 333968-48-2
benzyl N-acetyl-{4-[3,5-bis(tert-butyldimethylsilyloxy)-2-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentyl]butylamino}acetate

Guidance literature:: Multi-step reaction with 5 steps

1: 2.43 g / imidazole / dimethylformamide / 36 h / 20 °C

2: 89 percent / H₂ / Pd/C / ethyl acetate / 48 h / 20 °C

3: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.75 h / -78 - 0 °C

4: 66 percent / NaCNBH₃; Et₃N / methanol; diethyl ether / 0.17 h / 20 °C

5: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; dmap; oxalyl dichloride; hydrogen; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 3: Swern oxidation;
DOI:10.1021/ol015613a

Reference yield:

: 150686-70-7
(R)-4-((tert-butyldimethylsilyl)oxy)-2-iodocyclopent-2-en-1-one

: 333968-48-2
benzyl N-acetyl-{4-[3,5-bis(tert-butyldimethylsilyloxy)-2-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentyl]butylamino}acetate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

1.2: 70 percent / K₃PO₄ / PdCl₂(dppf) / tetrahydrofuran; dimethylformamide; H₂O / 0.5 h / 20 °C

2.1: tert-BuLi; (2-thienyl)Cu(CN)Li / pentane; diethyl ether; tetrahydrofuran / -78 - -40 °C

2.2: 83 percent / diethyl ether; tetrahydrofuran; pentane / -78 - -20 °C

3.1: L-Selectride / tetrahydrofuran / 4 h / -78 °C

4.1: 2.43 g / imidazole / dimethylformamide / 36 h / 20 °C

5.1: 89 percent / H₂ / Pd/C / ethyl acetate / 48 h / 20 °C

6.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.75 h / -78 - 0 °C

7.1: 66 percent / NaCNBH₃; Et₃N / methanol; diethyl ether / 0.17 h / 20 °C

8.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; dmap; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; hydrogen; tert.-butyl lithium; L-Selectride; sodium cyanoborohydride; dimethyl sulfoxide; thien-2-yl(cyano)copper lithium; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; pentane; 6.1: Swern oxidation;
DOI:10.1021/ol015613a