(2R,3R,4S)-3-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-2,4-dimethyl-octadecanoic acid

Base Information

Chemical Name:(2R,3R,4S)-3-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-2,4-dimethyl-octadecanoic acid
CAS No.:870192-76-0
Molecular Formula:C₄₄H₇₅N₃O₁₀
Molecular Weight:806.094
Hs Code.:

(2R,3R,4S)-3-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-2,4-dimethyl-octadecanoic acid

Synonyms:(2R,3R,4S)-3-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-2,4-dimethyl-octadecanoic acid

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Chemical Property of (2R,3R,4S)-3-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-2,4-dimethyl-octadecanoic acid

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Technology Process of (2R,3R,4S)-3-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-2,4-dimethyl-octadecanoic acid

There total 10 articles about (2R,3R,4S)-3-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-2,4-dimethyl-octadecanoic 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:

: 845521-50-8
N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-L-threonyl-O-(phenylmethyl)-L-serine (1R,2S)-1-[(1S)-2-hydroxy-1-methylethyl]-2-methylhexadecyl ester

: 870192-76-0
(2R,3R,4S)-3-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-2,4-dimethyl-octadecanoic acid

Guidance literature:: N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-L-threonyl-O-(phenylmethyl)-L-serine (1R,2S)-1-[(1S)-2-hydroxy-1-methylethyl]-2-methylhexadecyl ester; With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium bromide; In dichloromethane; water; at 0 ℃;

With sodium chlorite; sodium dihydrogenphosphate; amidosulfuric acid fluoride; In water; tert-butyl alcohol; at 0 ℃;
DOI:10.1016/j.tetlet.2004.11.121

Reference yield:

: 870192-69-1
(S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-dihydroxy-2,4-dimethyl-pentyl ester

: 870192-76-0
(2R,3R,4S)-3-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-2,4-dimethyl-octadecanoic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: 95 percent / imidazole / dimethylformamide / 0.25 h / 25 °C

2.1: 50 percent / LHMDS / tetrahydrofuran / 0.17 h / -40 °C

3.1: KBr; NaHCO₃; aq. NaClO / TEMPO / CH₂Cl₂ / 0.75 h / 0 °C

4.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

4.2: tetrahydrofuran / 0.25 h

5.1: H₂; ethylenediamine / Pd/C / methanol / 0.5 h / 25 °C

6.1: HOBt; EDCI / dimethylformamide / 0.5 h / 25 °C

7.1: 90 percent / aq. acetic acid / tetrahydrofuran / 18 h / 25 °C

8.1: KBr; NaHCO₃; aq. NaClO / TEMPO / CH₂Cl₂ / 1 h / 0 °C

8.2: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 1 h / 25 °C

With 1H-imidazole; sodium hypochlorite; hydrogen; sodium hexamethyldisilazane; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethylenediamine; potassium bromide; lithium hexamethyldisilazane; 2,2,6,6-tetramethyl-piperidine-N-oxyl; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4.2: Wittig reaction;
DOI:10.1016/j.tetlet.2005.09.037

Reference yield:

: 870192-72-6
(S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (1S,2S)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-1-((R)-1-methyl-2-oxo-ethyl)-propyl ester

: 870192-76-0
(2R,3R,4S)-3-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-2,4-dimethyl-octadecanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

1.2: tetrahydrofuran / 0.25 h

2.1: H₂; ethylenediamine / Pd/C / methanol / 0.5 h / 25 °C

3.1: HOBt; EDCI / dimethylformamide / 0.5 h / 25 °C

4.1: 90 percent / aq. acetic acid / tetrahydrofuran / 18 h / 25 °C

5.1: KBr; NaHCO₃; aq. NaClO / TEMPO / CH₂Cl₂ / 1 h / 0 °C

5.2: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 1 h / 25 °C

With sodium hypochlorite; hydrogen; sodium hexamethyldisilazane; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethylenediamine; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.2: Wittig reaction;
DOI:10.1016/j.tetlet.2005.09.037