methyl (2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>prolinate

Base Information

Chemical Name:methyl (2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>prolinate
CAS No.:128854-38-6
Molecular Formula:C₁₈H₂₂N₂O₅
Molecular Weight:346.383
Hs Code.:

Synonyms:methyl (2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>prolinate

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Chemical Property of methyl (2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>prolinate

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Technology Process of methyl (2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>prolinate

There total 9 articles about methyl (2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>prolinate 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: 87.0%

: 67-56-1
methanol

: 144610-82-2
(2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>proline

: 128854-38-6
methyl (2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>prolinate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1016/S0040-4039(01)93413-6

Reference yield:

: 144610-81-1
(2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>prolinal

: 128854-38-6
methyl (2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>prolinate

Guidance literature:: Multi-step reaction with 2 steps

1: 93.5 percent / 1.25 M NaHPO₄*H₂O buffer, 1 M aq. KMnO₄ / 2-methyl-propan-2-ol; CH₂Cl₂

2: 81 percent / 4-(N,N-dimethylamino)pyridine, dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 3 h

With dmap; potassium permanganate; NaHPO₄*H₂O buffer; dicyclohexyl-carbodiimide; In dichloromethane; tert-butyl alcohol;
DOI:10.1021/ja00052a015

Reference yield:

: 144610-79-7
(2R,3S)-3-(4-cyanophenoxy)-2-<<((1,1-dimethylethyl)dimethylsilyl)oxy>methyl>-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine

: 128854-38-6
methyl (2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>prolinate

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / aq. AcOH / tetrahydrofuran / 18 h / 45 °C

2: 85 percent / DMSO, trifluoroacid anhydride (TFAA), Et₃N / CH₂Cl₂ / -78 - 25 °C

3: 93.5 percent / 1.25 M NaHPO₄*H₂O buffer, 1 M aq. KMnO₄ / 2-methyl-propan-2-ol; CH₂Cl₂

4: 81 percent / 4-(N,N-dimethylamino)pyridine, dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 3 h

With dmap; potassium permanganate; NaHPO₄*H₂O buffer; trifluoroacid anhydride; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;
DOI:10.1021/ja00052a015