[(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-hydroxybutyl]carbamic acid tert-butyl ester

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Chemical Name:[(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-hydroxybutyl]carbamic acid tert-butyl ester
CAS No.:817167-02-5
Molecular Formula:C₂₀H₂₉NO₅
Molecular Weight:363.454
Hs Code.:

Synonyms:[(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-hydroxybutyl]carbamic acid tert-butyl ester

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Chemical Property of [(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-hydroxybutyl]carbamic acid tert-butyl ester

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Technology Process of [(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-hydroxybutyl]carbamic acid tert-butyl ester

There total 12 articles about [(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-hydroxybutyl]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: 76.0%

: 817166-95-3
[(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-(tert-butyldimethylsilanyloxy)butyl]carbamic acid tert-butyl ester

: 817167-02-5
[(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-hydroxybutyl]carbamic acid tert-butyl ester

Guidance literature:: With acetic acid; In tetrahydrofuran; at 20 ℃; for 3h;
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

: 817167-02-5
[(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-hydroxybutyl]carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 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: 76 percent / aq. AcOH / tetrahydrofuran / 3 h / 20 °C

With hydrogen; acetic anhydride; acetic acid; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; ethyl acetate;
DOI:10.1021/ol047879y

Reference yield:

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

: 817167-02-5
[(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-hydroxybutyl]carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 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: 76 percent / aq. AcOH / tetrahydrofuran / 3 h / 20 °C

With hydrogen; acetic anhydride; acetic acid; lithium tri-t-butoxyaluminum hydride; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; ethyl acetate; toluene;
DOI:10.1021/ol047879y