[(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-3-(2,4,6-trimethoxybenzylcarbamoyl)propyl]carbamic acid tert-butyl ester

Base Information

Chemical Name:[(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-3-(2,4,6-trimethoxybenzylcarbamoyl)propyl]carbamic acid tert-butyl ester
CAS No.:817167-07-0
Molecular Formula:C₃₀H₄₀N₂O₈
Molecular Weight:556.656
Hs Code.:

Synonyms:[(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-3-(2,4,6-trimethoxybenzylcarbamoyl)propyl]carbamic acid tert-butyl ester

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Chemical Property of [(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-3-(2,4,6-trimethoxybenzylcarbamoyl)propyl]carbamic acid tert-butyl ester

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Technology Process of [(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-3-(2,4,6-trimethoxybenzylcarbamoyl)propyl]carbamic acid tert-butyl ester

There total 16 articles about [(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-3-(2,4,6-trimethoxybenzylcarbamoyl)propyl]carbamic 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: 95.0%

: 817167-06-9
C₃₅H₄₈N₂O₁₀

: 817167-07-0
[(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-3-(2,4,6-trimethoxybenzylcarbamoyl)propyl]carbamic acid tert-butyl ester

Guidance literature:: With lithium bromide; In acetonitrile; at 65 ℃;
DOI:10.1021/ol047879y

Reference yield:

: 817166-96-4
[4-(tert-butyldimethylsilanyloxy)-(1S)-1-(5-oxotetrahydrofuran-(2R)-2-yl)butyl]carbamic acid tert-butyl ester

: 817167-07-0
[(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-3-(2,4,6-trimethoxybenzylcarbamoyl)propyl]carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: LDA / tetrahydrofuran; hexane / 3.5 h / -78 °C

2: Ac₂O; Et₃N / 1.25 h / Heating

3: 0.790 g / H₂ / Pd/C / ethyl acetate; methanol / 4.25 h

4: 92 percent / DMAP / tetrahydrofuran / 21 h / Heating

5: 78 percent / CrO₃; H₂SO₄ / acetone / 1.5 h / -10 °C

6: 92 percent / 1-HOBt; diisopropylethylamine; HBTU / dimethylformamide / 0 - 20 °C

7: 95 percent / LiBr / acetonitrile / 65 °C

With chromium(VI) oxide; dmap; sulfuric acid; hydrogen; acetic anhydride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium bromide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; 5: Jones oxidation;
DOI:10.1021/ol047879y

Reference yield:

: 5-tert-butoxycarbonylamino-8-(tert-butyl-dimethyl-silanyloxy)-4-oxo-oct-2-enoic acid methyl ester

: 817167-07-0
[(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-3-(2,4,6-trimethoxybenzylcarbamoyl)propyl]carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 1.44 g / H₂ / Pd/C / ethyl acetate / 4 h

2: LiAlH(t-BuO)3 / ethanol / 2.5 h / -78 °C

3: 2.909 g / AcOH / toluene / 3 h / Heating

4: LDA / tetrahydrofuran; hexane / 3.5 h / -78 °C

5: Ac₂O; Et₃N / 1.25 h / Heating

6: 0.790 g / H₂ / Pd/C / ethyl acetate; methanol / 4.25 h

7: 92 percent / DMAP / tetrahydrofuran / 21 h / Heating

8: 78 percent / CrO₃; H₂SO₄ / acetone / 1.5 h / -10 °C

9: 92 percent / 1-HOBt; diisopropylethylamine; HBTU / dimethylformamide / 0 - 20 °C

10: 95 percent / LiBr / acetonitrile / 65 °C

With chromium(VI) oxide; dmap; sulfuric acid; hydrogen; acetic anhydride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; lithium tri-t-butoxyaluminum hydride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium bromide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 8: Jones oxidation;
DOI:10.1021/ol047879y