(S)-N-((1S,2S,4R)-1-Benzyl-2,7-dihydroxy-4-isobutylcarbamoyl-heptyl)-2-tert-butoxycarbonylamino-succinamic acid benzyl ester

Base Information

Chemical Name:(S)-N-((1S,2S,4R)-1-Benzyl-2,7-dihydroxy-4-isobutylcarbamoyl-heptyl)-2-tert-butoxycarbonylamino-succinamic acid benzyl ester
CAS No.:674787-27-0
Molecular Formula:C₃₅H₅₁N₃O₈
Molecular Weight:641.805
Hs Code.:

Synonyms:(S)-N-((1S,2S,4R)-1-Benzyl-2,7-dihydroxy-4-isobutylcarbamoyl-heptyl)-2-tert-butoxycarbonylamino-succinamic acid benzyl ester

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Chemical Property of (S)-N-((1S,2S,4R)-1-Benzyl-2,7-dihydroxy-4-isobutylcarbamoyl-heptyl)-2-tert-butoxycarbonylamino-succinamic acid benzyl ester

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Technology Process of (S)-N-((1S,2S,4R)-1-Benzyl-2,7-dihydroxy-4-isobutylcarbamoyl-heptyl)-2-tert-butoxycarbonylamino-succinamic acid benzyl ester

There total 4 articles about (S)-N-((1S,2S,4R)-1-Benzyl-2,7-dihydroxy-4-isobutylcarbamoyl-heptyl)-2-tert-butoxycarbonylamino-succinamic acid benzyl 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:

: 137281-77-7
{(1S)-1-[(4R)-4-allyl-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

: 674787-27-0
(S)-N-((1S,2S,4R)-1-Benzyl-2,7-dihydroxy-4-isobutylcarbamoyl-heptyl)-2-tert-butoxycarbonylamino-succinamic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: Rh(PPh₃)3; catechol borane / tetrahydrofuran / 1.5 h / 20 °C

1.2: 73 percent / aq. H₂O₂; KH₂PO₄ / tetrahydrofuran; ethanol / 12 h / 20 °C / pH 7.2

2.1: imidazole / dimethylformamide / 12 h / 20 °C

3.1: aq. NaOH / dioxane / 0.5 h

4.1: EDT; HOBt; NMM / dimethylformamide / 20 h

5.1: HCl / ethyl acetate / 0.33 h / -20 - 0 °C

6.1: EDT; HOBt; NMM / dimethylformamide / 20 h

With 4-methyl-morpholine; 1H-imidazole; hydrogenchloride; sodium hydroxide; 3>; ethylenediaminetetraacetic acid; benzotriazol-1-ol; benzo[1,3,2]dioxaborole; In tetrahydrofuran; 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2003.11.061

Reference yield:

: 333405-32-6
{(1S)-1-[(4R)-4-(3-hydroxy-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

: 674787-27-0
(S)-N-((1S,2S,4R)-1-Benzyl-2,7-dihydroxy-4-isobutylcarbamoyl-heptyl)-2-tert-butoxycarbonylamino-succinamic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: imidazole / dimethylformamide / 12 h / 20 °C

2: aq. NaOH / dioxane / 0.5 h

3: EDT; HOBt; NMM / dimethylformamide / 20 h

4: HCl / ethyl acetate / 0.33 h / -20 - 0 °C

5: EDT; HOBt; NMM / dimethylformamide / 20 h

With 4-methyl-morpholine; 1H-imidazole; hydrogenchloride; sodium hydroxide; ethylenediaminetetraacetic acid; benzotriazol-1-ol; In 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2003.11.061

Reference yield:

: (1-{4-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-5-oxo-tetrahydro-furan-2-yl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester

: 674787-27-0
(S)-N-((1S,2S,4R)-1-Benzyl-2,7-dihydroxy-4-isobutylcarbamoyl-heptyl)-2-tert-butoxycarbonylamino-succinamic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: aq. NaOH / dioxane / 0.5 h

2: EDT; HOBt; NMM / dimethylformamide / 20 h

3: HCl / ethyl acetate / 0.33 h / -20 - 0 °C

4: EDT; HOBt; NMM / dimethylformamide / 20 h

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; ethylenediaminetetraacetic acid; benzotriazol-1-ol; In 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2003.11.061