((R)-1-((S)-2-acetamido-4-((3-(benzyloxy)-2-((benzyloxy)methyl)propyl)amino)-4-oxobutanamido)-3-methylbutyl)boronic acid

Base Information

Chemical Name:((R)-1-((S)-2-acetamido-4-((3-(benzyloxy)-2-((benzyloxy)methyl)propyl)amino)-4-oxobutanamido)-3-methylbutyl)boronic acid
CAS No.:1564251-52-0
Molecular Formula:C₂₉H₄₂BN₃O₇
Molecular Weight:555.479
Hs Code.:

Synonyms:((R)-1-((S)-2-acetamido-4-((3-(benzyloxy)-2-((benzyloxy)methyl)propyl)amino)-4-oxobutanamido)-3-methylbutyl)boronic acid

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Chemical Property of ((R)-1-((S)-2-acetamido-4-((3-(benzyloxy)-2-((benzyloxy)methyl)propyl)amino)-4-oxobutanamido)-3-methylbutyl)boronic acid

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Technology Process of ((R)-1-((S)-2-acetamido-4-((3-(benzyloxy)-2-((benzyloxy)methyl)propyl)amino)-4-oxobutanamido)-3-methylbutyl)boronic acid

There total 9 articles about ((R)-1-((S)-2-acetamido-4-((3-(benzyloxy)-2-((benzyloxy)methyl)propyl)amino)-4-oxobutanamido)-3-methylbutyl)boronic 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: 87.0%

: 1564251-46-2
(S)-2-acetamido-N⁴-(3-(benzyloxy)-2-((benzyloxy)methyl)propyl)-N¹-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)succinamide

: 1564251-52-0
((R)-1-((S)-2-acetamido-4-((3-(benzyloxy)-2-((benzyloxy)methyl)propyl)amino)-4-oxobutanamido)-3-methylbutyl)boronic acid

Guidance literature:: With hydrogenchloride; Dihydroxy-isobutyl-boran; In methanol; hexane; water; at 20 ℃; for 24h;
DOI:10.1021/jm500045x

Reference yield:

: 99776-34-8
4-benzyloxy-3-benzyloxymethylbutyraldehyde

: 1564251-52-0
((R)-1-((S)-2-acetamido-4-((3-(benzyloxy)-2-((benzyloxy)methyl)propyl)amino)-4-oxobutanamido)-3-methylbutyl)boronic acid

Guidance literature:: Multi-step reaction with 6 steps

1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tetrahydrofuran; tert-butyl alcohol / 0.67 h

2: diphenyl phosphoryl azide; triethylamine / dichloromethane / 2 h / 0 - 20 °C

3: 34 h / Reflux

4: trifluoroacetic acid / dichloromethane / 10 h

5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / Cooling

6: hydrogenchloride; Dihydroxy-isobutyl-boran / methanol; water; hexane / 24 h / 20 °C

With hydrogenchloride; sodium chlorite; 1-hydroxy-7-aza-benzotriazole; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; Dihydroxy-isobutyl-boran; diphenyl phosphoryl azide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jm500045x

Reference yield:

: 1564251-59-7
C₃₁H₄₇BN₂O₇

: 1564251-52-0
((R)-1-((S)-2-acetamido-4-((3-(benzyloxy)-2-((benzyloxy)methyl)propyl)amino)-4-oxobutanamido)-3-methylbutyl)boronic acid

Guidance literature:: Multi-step reaction with 5 steps

1: trifluoroacetic acid / dichloromethane / 15 h / 0 - 20 °C

2: triethylamine / dichloromethane / 0.42 h / 0 - 20 °C

3: hydrogen; palladium on activated charcoal / tetrahydrofuran / 3 h

4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / Cooling

5: hydrogenchloride; Dihydroxy-isobutyl-boran / methanol; water; hexane / 24 h / 20 °C

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; Dihydroxy-isobutyl-boran; palladium on activated charcoal; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water;
DOI:10.1021/jm500045x