2-benzyl-2-[benzyloxycarbonyl(3-phenylprop-2-ynyl)amino]-5-methylhexa-3,4-dienoic acid tert-butyl ester

Base Information

Chemical Name:2-benzyl-2-[benzyloxycarbonyl(3-phenylprop-2-ynyl)amino]-5-methylhexa-3,4-dienoic acid tert-butyl ester
CAS No.:855334-37-1
Molecular Formula:C₃₅H₃₇NO₄
Molecular Weight:535.683
Hs Code.:

Synonyms:2-benzyl-2-[benzyloxycarbonyl(3-phenylprop-2-ynyl)amino]-5-methylhexa-3,4-dienoic acid tert-butyl ester

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Chemical Property of 2-benzyl-2-[benzyloxycarbonyl(3-phenylprop-2-ynyl)amino]-5-methylhexa-3,4-dienoic acid tert-butyl ester

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Technology Process of 2-benzyl-2-[benzyloxycarbonyl(3-phenylprop-2-ynyl)amino]-5-methylhexa-3,4-dienoic acid tert-butyl ester

There total 6 articles about 2-benzyl-2-[benzyloxycarbonyl(3-phenylprop-2-ynyl)amino]-5-methylhexa-3,4-dienoic acid tert-butyl 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: 90.0%

: 855334-35-9
2-benzyl-2-benzyloxycarbonylamino-5-methylhexa-3,4-dienoic acid tert-butyl ester

: 1794-48-5
1-bromo-3-phenylprop-2-yne

: 855334-37-1
2-benzyl-2-[benzyloxycarbonyl(3-phenylprop-2-ynyl)amino]-5-methylhexa-3,4-dienoic acid tert-butyl ester

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1021/jo0502596

Reference yield:

: 5272-33-3
2-methyl-4-(trimethylsilyl)but-3-yn-2-ol

: 855334-37-1
2-benzyl-2-[benzyloxycarbonyl(3-phenylprop-2-ynyl)amino]-5-methylhexa-3,4-dienoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 68 percent / DMAP; DCC / tetrahydrofuran / 14 h / 20 °C

2: ZnBr₂; lithium diisopropylamide / tetrahydrofuran; hexane / 14 h / -78 - 20 °C

3: BF₃*Et₂O / CH₂Cl₂ / 22 h / 20 °C

4: tetrabutylammonium fluoride; phosphate buffer / tetrahydrofuran; H₂O / 10 h / pH 7

5: 90 percent / NaH / various solvent(s); dimethylformamide / 1 h / 20 °C

With dmap; phosphate buffer; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; dicyclohexyl-carbodiimide; zinc dibromide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; 2: Claisen rearrangement;
DOI:10.1021/jo0502596

Reference yield:

: 2-benzyloxycarbonylamino-3-phenylpropionic acid 1,1-dimethyl-3-trimethylsilanylprop-2-ynyl ester

: 855334-37-1
2-benzyl-2-[benzyloxycarbonyl(3-phenylprop-2-ynyl)amino]-5-methylhexa-3,4-dienoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: ZnBr₂; lithium diisopropylamide / tetrahydrofuran; hexane / 14 h / -78 - 20 °C

2: BF₃*Et₂O / CH₂Cl₂ / 22 h / 20 °C

3: tetrabutylammonium fluoride; phosphate buffer / tetrahydrofuran; H₂O / 10 h / pH 7

4: 90 percent / NaH / various solvent(s); dimethylformamide / 1 h / 20 °C

With phosphate buffer; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; zinc dibromide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1: Claisen rearrangement;
DOI:10.1021/jo0502596