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

Base Information

• Chemical Name: 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
• CAS No.: 361433-04-7
• Molecular Formula: C₄₆H₆₉BrN₆O₁₃
• Molecular Weight: 993.99

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 2 articles about 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 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: 74.0%

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) + N-{2-[2-(2-tert-butoxycarbonylaminoethoxy)ethoxy]ethyl}acrylamide (361433-00-3) → 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 (361433-04-7) + N1,N6-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2,5-bis{4-[(E)-2-(N-{2-[2-(2-t-butoxycarbonylaminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-3,4-dihydroxyhexanediamide

Guidance literature:

With N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; palladium diacetate; In water; N,N-dimethyl-formamide; at 80 ℃; for 8h; in sealed tube;

DOI:10.1016/S0928-0987(01)00109-9

Reference yield:

tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate (153086-78-3) → 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 (361433-04-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / diisopropylethylamine / CH₂Cl₂ / 1 h / 20 °C

2: 15 percent / diisopropylethylamine; P(o-Tol)3 / Pd(OAc)2 / H₂O; dimethylformamide / 8 h / 80 °C / in sealed tube

With N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; palladium diacetate; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0928-0987(01)00109-9

Reference yield: 98.0%

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 (361433-04-7) → N1,N6-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-aminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide (361433-05-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.166667h;

DOI:10.1016/S0928-0987(01)00109-9

upstream raw materials:

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

N-{2-[2-(2-tert-butoxycarbonylaminoethoxy)ethoxy]ethyl}acrylamide

tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate

Downstream raw materials:

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

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