(S)-2-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-benzyloxy-butyrylamino]-3-benzyloxy-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-benzyloxy-butyrylamino]-3-benzyloxy-propionic acid methyl ester
• CAS No.: 864430-42-2
• Molecular Formula: C₂₇H₃₇N₃O₆
• Molecular Weight: 499.607

Synonyms:(S)-2-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-benzyloxy-butyrylamino]-3-benzyloxy-propionic acid methyl ester

Chemical Property of (S)-2-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-benzyloxy-butyrylamino]-3-benzyloxy-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (S)-2-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-benzyloxy-butyrylamino]-3-benzyloxy-propionic acid methyl ester

There total 1 articles about (S)-2-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-benzyloxy-butyrylamino]-3-benzyloxy-propionic 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:

(S)-3-Benzyloxy-2-[(2S,3R)-3-benzyloxy-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-butyrylamino]-propionic acid methyl ester → (S)-2-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-benzyloxy-butyrylamino]-3-benzyloxy-propionic acid methyl ester (864430-42-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃;

DOI:10.1016/j.tetlet.2005.06.073

Reference yield: 65.0%

(R)-2-((4R,5S,6R)-2,2,5-Trimethyl-6-tridecyl-[1,3]dioxan-4-yl)-propionic acid (864430-35-3) + (S)-2-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-benzyloxy-butyrylamino]-3-benzyloxy-propionic acid methyl ester (864430-42-2) → (S)-3-Benzyloxy-2-((2S,3R)-3-benzyloxy-2-{(S)-3-methyl-2-[(R)-2-((4R,5S,6R)-2,2,5-trimethyl-6-tridecyl-[1,3]dioxan-4-yl)-propionylamino]-butyrylamino}-butyrylamino)-propionic acid methyl ester (864430-44-4)

Guidance literature:

(R)-2-((4R,5S,6R)-2,2,5-Trimethyl-6-tridecyl-[1,3]dioxan-4-yl)-propionic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃;

(S)-2-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-benzyloxy-butyrylamino]-3-benzyloxy-propionic acid methyl ester; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 12h;

DOI:10.1016/j.tetlet.2005.06.073

Reference yield:

(S)-2-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-benzyloxy-butyrylamino]-3-benzyloxy-propionic acid methyl ester (864430-42-2) → (3S,6S,9S,12R,13R)-6-((R)-1-Benzyloxy-ethyl)-3-benzyloxymethyl-13-((1S,2R)-2-hydroxy-1-methyl-pentadecyl)-9-isopropyl-12-methyl-1-oxa-4,7,10-triaza-cyclotridecane-2,5,8,11-tetraone

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide*HCl; 1-hydroxybenzotriazole / CH₂Cl₂ / 0 °C

1.2: 65 percent / DIPEA / CH₂Cl₂ / 12 h / 0 - 20 °C

2.1: LiOH / tetrahydrofuran; methanol; H₂O / 1 h / 0 °C

3.1: DCC; DMAP / CH₂Cl₂ / 2 h / 0 °C

4.1: CSA / CH₂Cl₂ / 2 h / 0 - 20 °C

5.1: morpholine / Pd(Ph₃P)4 / tetrahydrofuran

6.1: 45 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / tetrahydrofuran / 0 - 20 °C

With morpholine; dmap; lithium hydroxide; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; 6.1: Yamaguchi macrolactonization;

DOI:10.1016/j.tetlet.2005.06.073

Downstream raw materials:

(S)-3-Benzyloxy-2-((2S,3R)-3-benzyloxy-2-{(S)-3-methyl-2-[(R)-2-((4R,5S,6R)-2,2,5-trimethyl-6-tridecyl-[1,3]dioxan-4-yl)-propionylamino]-butyrylamino}-butyrylamino)-propionic acid methyl ester

(2S)-3-(benzyloxy)-2-{[(2S)-3-(benzyloxy)-2-{[(2S)-2-{[(2R,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino}-3-methylbutanoyl]amino}butanoyl]amino}propanoic acid

prop-2-en-1-yl (2S)-3-(benzyloxy)-2-{[(2S)-3-(benzyloxy)-2-{[(2S)-2-{[(2R,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino}-3-methylbutanoyl]amino}butanoyl]amino}propanoate

(S)-3-Benzyloxy-2-((2S,3R)-3-benzyloxy-2-{(S)-3-methyl-2-[(R)-2-((4R,5S,6R)-2,2,5-trimethyl-6-tridecyl-[1,3]dioxan-4-yl)-propionylamino]-butyrylamino}-butyrylamino)-propionic acid allyl ester

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