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

Base Information

Chemical Name:(2R,3R,4S)-3-{(S)-2-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-3-benzyloxy-propionyloxy}-2,4-dimethyl-octadecanoic acid
CAS No.:845521-51-9
Molecular Formula:C₃₉H₆₇N₃O₈
Molecular Weight:705.976
Hs Code.:

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

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

Chemical Property:

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

There total 9 articles about (2R,3R,4S)-3-{(S)-2-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-3-benzyloxy-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:

: 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

: 845521-51-9
(2R,3R,4S)-3-{(S)-2-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-3-benzyloxy-propionyloxy}-2,4-dimethyl-octadecanoic acid

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/j.tetlet.2005.09.037

Reference yield:

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

: 845521-51-9
(2R,3R,4S)-3-{(S)-2-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-3-benzyloxy-propionyloxy}-2,4-dimethyl-octadecanoic acid

Guidance literature:: Multi-step reaction with 9 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

9.1: TFA / CH₂Cl₂ / 1 h / 0 °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; trifluoroacetic acid; 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:

: (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-diisopropoxy-2,4-dimethyl-pentyl ester

: 845521-51-9
(2R,3R,4S)-3-{(S)-2-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-3-benzyloxy-propionyloxy}-2,4-dimethyl-octadecanoic acid

Guidance literature:: Multi-step reaction with 10 steps

1.1: 95 percent / aq. acetic acid / tetrahydrofuran / 12 h / 25 °C

2.1: 95 percent / imidazole / dimethylformamide / 0.25 h / 25 °C

3.1: 50 percent / LHMDS / tetrahydrofuran / 0.17 h / -40 °C

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

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

5.2: tetrahydrofuran / 0.25 h

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

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

8.1: 90 percent / aq. acetic acid / tetrahydrofuran / 18 h / 25 °C

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

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

10.1: TFA / CH₂Cl₂ / 1 h / 0 °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; trifluoroacetic acid; potassium bromide; lithium hexamethyldisilazane; 2,2,6,6-tetramethyl-piperidine-N-oxyl; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 5.2: Wittig reaction;
DOI:10.1016/j.tetlet.2005.09.037