(3S,4R,5S)-4-((2S,3R)-3-Benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)-3-hydroxy-5-methyl-heptanoic acid methyl ester

Base Information

Chemical Name:(3S,4R,5S)-4-((2S,3R)-3-Benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)-3-hydroxy-5-methyl-heptanoic acid methyl ester
CAS No.:185461-64-7
Molecular Formula:C₂₅H₄₀N₂O₇
Molecular Weight:480.602
Hs Code.:

Synonyms:

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Chemical Property of (3S,4R,5S)-4-((2S,3R)-3-Benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)-3-hydroxy-5-methyl-heptanoic acid methyl ester

Chemical Property:

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Technology Process of (3S,4R,5S)-4-((2S,3R)-3-Benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)-3-hydroxy-5-methyl-heptanoic acid methyl ester

There total 2 articles about (3S,4R,5S)-4-((2S,3R)-3-Benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)-3-hydroxy-5-methyl-heptanoic acid methyl 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:

: 159407-38-2
(3S,4R,5S)-Boc-isostatine methyl ester

: 185461-64-7
(3S,4R,5S)-4-((2S,3R)-3-Benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)-3-hydroxy-5-methyl-heptanoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: TFA / CH₂Cl₂ / 0.33 h

2: 1-hydroxybenzotriazole, N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide, N,N-diisopropylethylamine / acetonitrile / 24 h / Ambient temperature

With N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; acetonitrile;
DOI:10.1021/jo961932h

Reference yield:

: 15260-10-3
N-Boc-O-benzyl-L-threonine

: (3S,4R,5S)-4-Amino-3-hydroxy-5-methyl-heptanoic acid methyl ester

: 185461-64-7
(3S,4R,5S)-4-((2S,3R)-3-Benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)-3-hydroxy-5-methyl-heptanoic acid methyl ester

Guidance literature:: With N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In acetonitrile; for 24h; Yield given; Ambient temperature;
DOI:10.1021/jo961932h

Reference yield:

: 185461-64-7
(3S,4R,5S)-4-((2S,3R)-3-Benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)-3-hydroxy-5-methyl-heptanoic acid methyl ester

: 137219-37-5
dehydrodidemnin B

Guidance literature:: Multi-step reaction with 14 steps

1: 5 M HCl / dioxane / 0.83 h

2: 1-hydroxybenzotriazole, (1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, N,N-diisopropylethylamine / dimethylformamide / 24 h / Ambient temperature

3: 96 percent / 1 M NaOH / methanol / 4 h / 0 °C

4: 72 percent / imidazole / dimethylformamide / 36 h

5: 80 percent / DCC, DMAP / CH₂Cl₂ / 24 h / Ambient temperature

6: 90 percent / H₂ / Pd/C / tetrahydrofuran / 1.5 h / 760 Torr / Ambient temperature

7: 79 percent / DCC, DMAP / CH₂Cl₂ / 24 h / Ambient temperature

8: 66 percent / Zn, aq. NH₄OAc / tetrahydrofuran / 24 h

9: 60 percent / DMAP*CF₃COOH, N,N'-diisopropylcarbodiimide / CHCl₃ / 1.) reflux, 8 h, 2.) room temperature, 16 h

10: 81 percent / aq. NH₄OAc, Zn / tetrahydrofuran / 24 h

11: 95 percent / H₂ / Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature

12: 28 percent / N-<(dimethylamino)-1H-1,2,3-triazolo<4,5-b>pyridin-1-ylmethylene>-N-methylmethanaminium hexafluorophosphate N-oxide, 1-hydroxy-7-azabenzotriazole, N,N-diisopropylethylamine / tetrahydrofuran / 3 h / 0 °C

13: 98 percent / 5 M HCl / dioxane / 1 h

14: 62 percent / bromotripyrrolidinophosphonium hexafluorophosphate, diisopropylethylamine / CH₂Cl₂ / 1.) -5 deg C, 30 min, 2.) room temperature, 4 h

With 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; N-<(dimethylamino)-1H-1,2,3-triazolo<4,5-b>pyridin-1-ylmethylene>-N-methylmethanaminium hexafluorophosphate N-oxide; ammonium acetate; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; 4-N,N-dimethylaminopyridine trifluoroacetate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; diisopropyl-carbodiimide; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jo961932h