cis,cis-3-tert-butyldimethylsilyloxy-4-acetamido-5-benzyloxycyclopentene

Base Information

Chemical Name:cis,cis-3-tert-butyldimethylsilyloxy-4-acetamido-5-benzyloxycyclopentene
CAS No.:791821-57-3
Molecular Formula:C₂₀H₃₁NO₃Si
Molecular Weight:361.557
Hs Code.:

Synonyms:cis,cis-3-tert-butyldimethylsilyloxy-4-acetamido-5-benzyloxycyclopentene

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Chemical Property of cis,cis-3-tert-butyldimethylsilyloxy-4-acetamido-5-benzyloxycyclopentene

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Technology Process of cis,cis-3-tert-butyldimethylsilyloxy-4-acetamido-5-benzyloxycyclopentene

There total 6 articles about cis,cis-3-tert-butyldimethylsilyloxy-4-acetamido-5-benzyloxycyclopentene 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: 85.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 791821-58-4
cis,cis-4-acetamido-5-benzyloxycyclopenten-3-ol

: 791821-57-3
cis,cis-3-tert-butyldimethylsilyloxy-4-acetamido-5-benzyloxycyclopentene

Guidance literature:: With 1H-imidazole; In dichloromethane; at 25 ℃; for 12h;
DOI:10.1021/jo040226a

Reference yield:

: 100-39-0
benzyl bromide

: 791821-57-3
cis,cis-3-tert-butyldimethylsilyloxy-4-acetamido-5-benzyloxycyclopentene

Guidance literature:: Multi-step reaction with 4 steps

1.1: 94 percent / NaH / dimethylformamide / 2 h / 25 °C

2.1: 100 percent / TBAF / tetrahydrofuran / 3 h / 25 °C

3.1: Burgess reagent / tetrahydrofuran / 3 h / 70 °C

3.2: 77 percent / aq. NaH₂PO₄ / tetrahydrofuran / 12 h / 25 °C

4.1: 85 percent / imidazole / CH₂Cl₂ / 12 h / 25 °C

With 1H-imidazole; Burgess Reagent; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo040226a

Reference yield:

: 213406-16-7
(1S,4R,5R)-5-acetylamino-4-tert-butyldimethylsilyloxy-2-cyclopenten-1-ol

: 791821-57-3
cis,cis-3-tert-butyldimethylsilyloxy-4-acetamido-5-benzyloxycyclopentene

Guidance literature:: Multi-step reaction with 5 steps

1.1: Burgess reagent / tetrahydrofuran / 3 h / 70 °C

1.2: 76 percent / aq. NaH₂PO₄ / tetrahydrofuran / 72 h / 25 °C

2.1: 94 percent / NaH / dimethylformamide / 2 h / 25 °C

3.1: 100 percent / TBAF / tetrahydrofuran / 3 h / 25 °C

4.1: Burgess reagent / tetrahydrofuran / 3 h / 70 °C

4.2: 77 percent / aq. NaH₂PO₄ / tetrahydrofuran / 12 h / 25 °C

5.1: 85 percent / imidazole / CH₂Cl₂ / 12 h / 25 °C

With 1H-imidazole; Burgess Reagent; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo040226a