N-tert-Butyl-1-[[(2S)-4beta-benzyl-5-oxotetrahydrofuran-2alpha-yl]methyl]-4-(tert-butoxycarbonyl)piperazine-2alpha-carboxamide

Base Information

Chemical Name:N-tert-Butyl-1-[[(2S)-4beta-benzyl-5-oxotetrahydrofuran-2alpha-yl]methyl]-4-(tert-butoxycarbonyl)piperazine-2alpha-carboxamide
CAS No.:150323-36-7
Molecular Formula:C₂₆H₃₉N₃O₅
Molecular Weight:473.613
Hs Code.:
DSSTox Substance ID:DTXSID401099517
Nikkaji Number:J1.356.570H

N-tert-Butyl-1-[[(2S)-4beta-benzyl-5-oxotetrahydrofuran-2alpha-yl]methyl]-4-(tert-butoxycarbonyl)piperazine-2alpha-carboxamide

Synonyms:DTXSID401099517;150323-36-7;D-erythro-Pentonic acid, 2,3,5-trideoxy-5-[(2S)-4-[(1,1-dimethylethoxy)carbonyl]-2-[[(1,1-dimethylethyl)amino]carbonyl]-1-piperazinyl]-2-(phenylmethyl)-, gamma-lactone;N-tert-Butyl-1-[[(2S)-4beta-benzyl-5-oxotetrahydrofuran-2alpha-yl]methyl]-4-(tert-butoxycarbonyl)piperazine-2alpha-carboxamide

Suppliers and Price of N-tert-Butyl-1-[[(2S)-4beta-benzyl-5-oxotetrahydrofuran-2alpha-yl]methyl]-4-(tert-butoxycarbonyl)piperazine-2alpha-carboxamide

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of N-tert-Butyl-1-[[(2S)-4beta-benzyl-5-oxotetrahydrofuran-2alpha-yl]methyl]-4-(tert-butoxycarbonyl)piperazine-2alpha-carboxamide

Chemical Property:

XLogP3:3.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:8
Exact Mass:473.28897135
Heavy Atom Count:34
Complexity:736

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC(C)(C)NC(=O)C1CN(CCN1CC2CC(C(=O)O2)CC3=CC=CC=C3)C(=O)OC(C)(C)C
Isomeric SMILES:CC(C)(C)NC(=O)[C@@H]1CN(CCN1C[C@@H]2C[C@H](C(=O)O2)CC3=CC=CC=C3)C(=O)OC(C)(C)C

Technology Process of N-tert-Butyl-1-[[(2S)-4beta-benzyl-5-oxotetrahydrofuran-2alpha-yl]methyl]-4-(tert-butoxycarbonyl)piperazine-2alpha-carboxamide

There total 9 articles about N-tert-Butyl-1-[[(2S)-4beta-benzyl-5-oxotetrahydrofuran-2alpha-yl]methyl]-4-(tert-butoxycarbonyl)piperazine-2alpha-carboxamide 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: 83.0%

: 150323-35-6,171866-36-7,128019-61-4
t-butyl (S)-3-(tert-butylcarbamoyl)-piperazine-1-carboxylate

: 150323-33-4
dihydro-5(S)-<<<(trifluoromethyl)sulfonyl>oxy>methyl>-3(R)-(phenylmethyl)-3(2H)-furanone

: 150323-36-7
dihydro-5(S)-<<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>methyl>-3(R)-(phenylmethyl)-3(2H)-furanone

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; for 3.5h;
DOI:10.1021/jm00047a001

Reference yield:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 150323-36-7
dihydro-5(S)-<<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>methyl>-3(R)-(phenylmethyl)-3(2H)-furanone

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / imidazole / CH₂Cl₂ / 4 h / 0 - 20 °C

2: 1.) LDA / 1.) THF, hexane, 30 min, 2.) THF, hexane, 3 h

3: 97 percent / 49percent aq. HF / acetonitrile / 18 h / Ambient temperature

4: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

5: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h

With 1H-imidazole; 2,6-dimethylpyridine; hydrogen fluoride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In dichloromethane; isopropyl alcohol; acetonitrile;
DOI:10.1021/jm00047a001

Reference yield:

: 58632-95-4
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

: 150323-36-7
dihydro-5(S)-<<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>methyl>-3(R)-(phenylmethyl)-3(2H)-furanone

Guidance literature:: Multi-step reaction with 5 steps

1: 40percent NaOH / dioxane; H₂O / 2.5 h

2: 40percent NaOH / dioxane; H₂O / 14 h

3: 85 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et₃N / dimethylformamide / 18 h

4: 96 percent / H₂ / 10percent Pd/C / methanol / 3 h

5: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h

With sodium hydroxide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jm00047a001