(2S,3S)-2-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanamido)-3-methylpentanoic acid

Base Information

• Chemical Name: (2S,3S)-2-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanamido)-3-methylpentanoic acid
• CAS No.: 1427166-49-1
• Molecular Formula: C₂₁H₃₂N₂O₆
• Molecular Weight: 408.495

Synonyms:(2S,3S)-2-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanamido)-3-methylpentanoic acid

Chemical Property of (2S,3S)-2-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanamido)-3-methylpentanoic acid

Chemical Property:

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Technology Process of (2S,3S)-2-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanamido)-3-methylpentanoic acid

There total 3 articles about (2S,3S)-2-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanamido)-3-methylpentanoic 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: 82.0%

Boc-Ser(Bn)-OH + L-isoleucine sodium salt → (2S,3S)-2-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanamido)-3-methylpentanoic acid (1427166-49-1)

Guidance literature:

Boc-Ser(Bn)-OH; With 4-methyl-morpholine; N-ethyl-N,N-diisopropylamine; isobutyl chloroformate; In acetonitrile; at 20 ℃; for 0.00138889h; Flow reactor;

L-isoleucine sodium salt; In water; acetonitrile; at 20 ℃; for 0.00277778h; Flow reactor;

DOI:10.1002/chem.201903531

Reference yield: 80.0%

(S)-tert-butyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-3-(benzyloxy)-1-oxopropan-2-yl)carbamate (1072841-05-4) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) → (2S,3S)-2-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanamido)-3-methylpentanoic acid (1427166-49-1)

Guidance literature:

With triethylamine; In water; acetonitrile; for 16h;

DOI:10.1039/c3cc39291k

Reference yield:

BOC-O-benzyl-L-serine (23680-31-1) → (2S,3S)-2-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanamido)-3-methylpentanoic acid (1427166-49-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dicyclohexyl-carbodiimide / dichloromethane / 0.5 h / Inert atmosphere

1.2: 12 h / 25 °C / Inert atmosphere

2.1: triethylamine / acetonitrile; water / 16 h

With triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; water; acetonitrile;

DOI:10.1039/c3cc39291k

upstream raw materials:

BOC-O-benzyl-L-serine

(S)-tert-butyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-3-(benzyloxy)-1-oxopropan-2-yl)carbamate

L-isoleucine

Downstream raw materials:

(6S,9S,12S,14aS,20S,23S,25aS)-20-benzyl-6,12-di((S)-sec-butyl)-9-(hydroxymethyl)-23-isobutylhexadecahydro-1H-dipyrrolo[1,2-a:1',2'-j][1,4,7,10,13,16,19]heptaazacyclohenicosine-5,8,11,14,19,22,25(25aH)heptaone

(S)-3-(benzyloxy)-1-(((1S,2S)-1-carboxy-2-methylbutyl)amino)-1-oxopropan-2-aminium chloride

(S)-1-((S)-2-((S)-2-((S)-1-((6S,9S,12S)-9-((benzyloxy)methyl)-6,12-di((S)-sec-butyl)-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oyl)pyrrolidine-2-carboxamido)-4-methylpentanamido)-3-phenylpropanoyl)pyrrolidine-2-carboxylic acid

(2S,3S)-1-(((S)-3-(benzyloxy)-1-(((2S,3S)-1-((S)-2-(((S)-1-(((S)-1-((S)-2-carboxypyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)carbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxopentan-2-yl)amino)-1-oxopropan-2-yl)amino)-3-methyl-1-oxopentan-2-aminium chloride

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