(4S,5S)-5-<1-(t-Boc-amino)-2-phenylethyl>-3-carbethoxy-3-(phenylmethyl)dihydrofuran-2(3H)-one

Base Information

Chemical Name:(4S,5S)-5-<1-(t-Boc-amino)-2-phenylethyl>-3-carbethoxy-3-(phenylmethyl)dihydrofuran-2(3H)-one
CAS No.:193339-06-9
Molecular Formula:C₂₇H₃₃NO₆
Molecular Weight:467.562
Hs Code.:

Synonyms:(4S,5S)-5-<1-(t-Boc-amino)-2-phenylethyl>-3-carbethoxy-3-(phenylmethyl)dihydrofuran-2(3H)-one

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Chemical Property of (4S,5S)-5-<1-(t-Boc-amino)-2-phenylethyl>-3-carbethoxy-3-(phenylmethyl)dihydrofuran-2(3H)-one

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Technology Process of (4S,5S)-5-<1-(t-Boc-amino)-2-phenylethyl>-3-carbethoxy-3-(phenylmethyl)dihydrofuran-2(3H)-one

There total 1 articles about (4S,5S)-5-<1-(t-Boc-amino)-2-phenylethyl>-3-carbethoxy-3-(phenylmethyl)dihydrofuran-2(3H)-one 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:

: 100-39-0
benzyl bromide

: 193338-94-2
(5S,1'S)-carbetoxy-5-<1-<<(1',1-dimethylothoxy)carbonyl>amino>-2-phenylmethyl>dihydrofuran-2(3H)-one

: 193339-06-9
(4S,5S)-5-<1-(t-Boc-amino)-2-phenylethyl>-3-carbethoxy-3-(phenylmethyl)dihydrofuran-2(3H)-one

Guidance literature:: With sodium ethanolate; In ethanol; for 18h; Ambient temperature;
DOI:10.1021/jm00088a004

Reference yield:

: 193339-06-9
(4S,5S)-5-<1-(t-Boc-amino)-2-phenylethyl>-3-carbethoxy-3-(phenylmethyl)dihydrofuran-2(3H)-one

: (S)-3-Benzyl-5-((S)-1-tert-butoxycarbonylamino-2-phenyl-ethyl)-2-oxo-tetrahydro-furan-3-carboxylic acid

Guidance literature:: With lithium hydroxide; In ethanol; for 5h;
DOI:10.1021/jm00088a004

Reference yield:

: 193339-06-9
(4S,5S)-5-<1-(t-Boc-amino)-2-phenylethyl>-3-carbethoxy-3-(phenylmethyl)dihydrofuran-2(3H)-one

: ((S)-1-{(S)-1-[(S)-1-((S)-4-Benzyl-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 3.3 g / pH buffer 10. 1N aq. NaOH / dioxane / 3 h

2: 78 percent / 0.5 h / 120 °C

3: 5.9 g / 1M aq. NaOH / dioxane / 0.5 h

4: imidazole / dimethylformamide / 18 h / Ambient temperature

5: aq. acetic acid / tetrahydrofuran / 1.5 h / Ambient temperature

6: HBT, EDC, triethylamine / dimethylformamide / 3 h / Ambient temperature

7: tetrabutylammonium fluoride / tetrahydrofuran / 40 h / Ambient temperature

8: 1.) HCl(gas), 2.) EDC, HBT, triethylamine / 1.) EtOAc, 0 deg C, 15 min, 2.) DMF, RT, 40 h

9: HCl(gas) / ethyl acetate

10: EDC, HBT, triethylamine / dimethylformamide / 2 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium hydroxide; pH buffer 10. 1N aq. NaOH; tetrabutyl ammonium fluoride; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo00223a037