(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester

Base Information

Chemical Name:(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester
CAS No.:81135-33-3
Molecular Formula:C₄₆H₇₇N₇O₉
Molecular Weight:872.159
Hs Code.:

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester

Synonyms:(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester

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Chemical Property of (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester

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Technology Process of (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester

There total 32 articles about (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine 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: 89.0%

: 81135-32-2
(4S,5R,1'R,3'E)-2,2,3-trimethyl-5-(1'-methyl-3'-pentenyl)-4-(oxazolidinylcarbonyl)-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester

: 81135-33-3
(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester

Guidance literature:: With hydrogenchloride; In methanol; for 12h; Ambient temperature;
DOI:10.1021/jo00296a061

Reference yield:

: 81135-22-0
N-(tert-Butyloxycarbonyl)-α-aminobutyrylsarcosine benzyl ester

: 81135-33-3
(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / hydrogen / 10 percent Pd-C / ethanol

2: diisopropylethylamine, N,N'-bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH₂Cl₂ / 5 h / 0 °C

3: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 14 h / -15 °C

4: 1) N-methylmorpholine, 1-hydroxybenzotriazole; 2) DCC / 1) THF; 2) 0 deg C, then 14 h room temperatur

5: 89 percent / 1.0 M aq. HCl / methanol / 12 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane;
DOI:10.1021/jo00296a061

Reference yield:

: 81135-24-2
N-(tert-butoxycarbonyl)-N-methyl-L-leucyl-L-alanine benzyl ester

: 81135-33-3
(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 50 percent trifluoroacetic acid / CH₂Cl₂ / 100 h / -18 - -13 °C

2: 78 percent / diisopropylethylamine, N,N'-bis(2-oxo-3-oxazolidinyl)phosphonic chloride / CH₂Cl₂ / 14 h / 5 °C

3: 100 percent / anisol, 5.8 M anhydrous HCl / dioxane / 1) 0 deg C, 2 h; 2) 5 deg C, 12 h

4: 1) diisopropylethylamine, N,N'-bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 2) diisopropylethylamine / 1) CH₂Cl₂, 0 deg C, 2 h; 2) CH₂Cl₂, 6 deg C

5: 86 percent / trifluoroacetic acid / CH₂Cl₂ / 29 h / -18 - -13 °C / or from Fmoc-MeLeu-Val-MeLeu-Ala-OBzl with diethylamine in CH₃CN

6: diisopropylethylamine, N,N'-bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH₂Cl₂ / 5 h / 0 °C

7: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 14 h / -15 °C

8: 1) N-methylmorpholine, 1-hydroxybenzotriazole; 2) DCC / 1) THF; 2) 0 deg C, then 14 h room temperatur

9: 89 percent / 1.0 M aq. HCl / methanol / 12 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; bis(2-oxo-3-oxazolidinyl)phosphoric acid chloride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; benzotriazol-1-ol; methoxybenzene; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In 1,4-dioxane; methanol; dichloromethane;
DOI:10.1021/jo00296a061