N₁,N₆-di[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2,5-di[(4-bromobenzyl)oxy]-3,4-dihydroxyhexanediamide

Base Information

• Chemical Name: N₁,N₆-di[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2,5-di[(4-bromobenzyl)oxy]-3,4-dihydroxyhexanediamide
• CAS No.: 214139-74-9
• Molecular Formula: C₃₂H₄₄Br₂N₄O₈
• Molecular Weight: 772.531

Synonyms:N₁,N₆-di[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2,5-di[(4-bromobenzyl)oxy]-3,4-dihydroxyhexanediamide

Chemical Property of N₁,N₆-di[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2,5-di[(4-bromobenzyl)oxy]-3,4-dihydroxyhexanediamide

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of N₁,N₆-di[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2,5-di[(4-bromobenzyl)oxy]-3,4-dihydroxyhexanediamide

There total 5 articles about N₁,N₆-di[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2,5-di[(4-bromobenzyl)oxy]-3,4-dihydroxyhexanediamide 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: 64.0%

L-valine N-methylamide (87105-26-8) + 2,5-O-bis(4-bromobenzyl)-L-mannaro-1,4:3,6-dilactone (214139-73-8) → N1,N6-di[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2,5-di[(4-bromobenzyl)oxy]-3,4-dihydroxyhexanediamide (214139-74-9)

Guidance literature:

In 1,2-dichloro-ethane; at 50 ℃; for 48h;

DOI:10.1021/jm9910371

Reference yield:

4-bromobenzenemethanol (873-75-6) → N1,N6-di[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2,5-di[(4-bromobenzyl)oxy]-3,4-dihydroxyhexanediamide (214139-74-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: toluene / 0.33 h

1.2: 25 percent / 1 h / 20 °C

2.1: 88 percent / triflic acid / dioxane / 2 h

3.1: 64 percent / 1,2-dichloro-ethane / 48 h / 50 °C

With trifluorormethanesulfonic acid; In 1,4-dioxane; 1,2-dichloro-ethane; toluene; 1.1: Metallation / 1.2: Addition / 2.1: Alkylation / 3.1: Addition;

DOI:10.1021/jm9910371

Reference yield:

(4-bromobenzyl)-2,2,2-trichloroacetimidate (146285-52-1) → N1,N6-di[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2,5-di[(4-bromobenzyl)oxy]-3,4-dihydroxyhexanediamide (214139-74-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / triflic acid / dioxane / 2 h

2: 64 percent / 1,2-dichloro-ethane / 48 h / 50 °C

With trifluorormethanesulfonic acid; In 1,4-dioxane; 1,2-dichloro-ethane; 1: Alkylation / 2: Addition;

DOI:10.1021/jm9910371

upstream raw materials:

L-valine N-methylamide

2,5-O-bis(4-bromobenzyl)-L-mannaro-1,4:3,6-dilactone

4-bromobenzenemethanol

(4-bromobenzyl)-2,2,2-trichloroacetimidate

Downstream raw materials:

N₁,N₆-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-t-butoxycarbonylaminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide

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