(4S)-4-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-[bis(tert-butoxycarbonyl)amino]butyric acid

Base Information

Chemical Name:(4S)-4-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-[bis(tert-butoxycarbonyl)amino]butyric acid
CAS No.:817167-05-8
Molecular Formula:C₂₅H₃₅NO₈
Molecular Weight:477.555
Hs Code.:

Synonyms:(4S)-4-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-[bis(tert-butoxycarbonyl)amino]butyric acid

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Chemical Property of (4S)-4-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-[bis(tert-butoxycarbonyl)amino]butyric acid

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Technology Process of (4S)-4-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-[bis(tert-butoxycarbonyl)amino]butyric acid

There total 13 articles about (4S)-4-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-[bis(tert-butoxycarbonyl)amino]butyric acid 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: 78.0%

: 817167-04-7
C₃₁H₅₁NO₇Si

: 817167-05-8
(4S)-4-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-[bis(tert-butoxycarbonyl)amino]butyric acid

Guidance literature:: With chromium(VI) oxide; sulfuric acid; In acetone; at -10 ℃; for 1.5h;
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

: 817167-05-8
(4S)-4-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-[bis(tert-butoxycarbonyl)amino]butyric acid

Guidance literature:: Multi-step reaction with 5 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

With chromium(VI) oxide; dmap; sulfuric acid; hydrogen; acetic anhydride; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; ethyl acetate; acetone; 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

: 817167-05-8
(4S)-4-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-[bis(tert-butoxycarbonyl)amino]butyric acid

Guidance literature:: Multi-step reaction with 8 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

With chromium(VI) oxide; dmap; sulfuric acid; 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; acetone; toluene; 8: Jones oxidation;
DOI:10.1021/ol047879y