(2R,3R)-4-benzylamino-2-(4-bromobenzyloxy)-N-(furan-2-yl-methyl)-3-hydroxy-butyramide

Base Information

Chemical Name:(2R,3R)-4-benzylamino-2-(4-bromobenzyloxy)-N-(furan-2-yl-methyl)-3-hydroxy-butyramide
CAS No.:639839-14-8
Molecular Formula:C₂₃H₂₅BrN₂O₄
Molecular Weight:473.366
Hs Code.:

Synonyms:(2R,3R)-4-benzylamino-2-(4-bromobenzyloxy)-N-(furan-2-yl-methyl)-3-hydroxy-butyramide

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Chemical Property of (2R,3R)-4-benzylamino-2-(4-bromobenzyloxy)-N-(furan-2-yl-methyl)-3-hydroxy-butyramide

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Technology Process of (2R,3R)-4-benzylamino-2-(4-bromobenzyloxy)-N-(furan-2-yl-methyl)-3-hydroxy-butyramide

There total 4 articles about (2R,3R)-4-benzylamino-2-(4-bromobenzyloxy)-N-(furan-2-yl-methyl)-3-hydroxy-butyramide 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: 90.0%

: 100-46-9
benzylamine

: 639839-06-8
(2R,3R)-2-(4-bromobenzyloxy)-3,4-epoxy-N-(furan-2-yl-methyl)-butyramide

: 639839-14-8
(2R,3R)-4-benzylamino-2-(4-bromobenzyloxy)-N-(furan-2-yl-methyl)-3-hydroxy-butyramide

Guidance literature:: In methanol; at 50 ℃; for 4h;
DOI:10.1016/S0968-0896(03)00312-2

Reference yield:

: 552887-04-4
methyl (2R,3R)-2-(4-bromobenzyloxy)-3,4-dihydroxy-3,4-O-isopropylidene-butyrate

: 639839-14-8
(2R,3R)-4-benzylamino-2-(4-bromobenzyloxy)-N-(furan-2-yl-methyl)-3-hydroxy-butyramide

Guidance literature:: Multi-step reaction with 5 steps

1: LiOH / dioxane; H₂O / 0.75 h / 0 °C

2: 1-hydroxybenzotriazole; Et₃N; N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride / dimethylformamide / 0 - 20 °C

3: Dowex H⁺ / methanol / 5 h / 20 °C

4: Ph₃P; diethylazodicarboxylate / CHCl₃ / 2 h / Heating

5: 90 percent / methanol / 4 h / 50 °C

With lithium hydroxide; Dowex H⁺; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; methanol; chloroform; water; N,N-dimethyl-formamide; 4: Mitsunobu reaction;
DOI:10.1016/S0968-0896(03)00312-2

Reference yield:

: (R)-(4-Bromo-benzyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetic acid

: 639839-14-8
(2R,3R)-4-benzylamino-2-(4-bromobenzyloxy)-N-(furan-2-yl-methyl)-3-hydroxy-butyramide

Guidance literature:: Multi-step reaction with 4 steps

1: 1-hydroxybenzotriazole; Et₃N; N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride / dimethylformamide / 0 - 20 °C

2: Dowex H⁺ / methanol / 5 h / 20 °C

3: Ph₃P; diethylazodicarboxylate / CHCl₃ / 2 h / Heating

4: 90 percent / methanol / 4 h / 50 °C

With Dowex H⁺; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In methanol; chloroform; N,N-dimethyl-formamide; 3: Mitsunobu reaction;
DOI:10.1016/S0968-0896(03)00312-2