(2S,3R)-1-(2-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)ethylamino)-3-hydroxy-1-oxobutan-2-aminium chloride

Base Information

Chemical Name:(2S,3R)-1-(2-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)ethylamino)-3-hydroxy-1-oxobutan-2-aminium chloride
CAS No.:1380092-51-2
Molecular Formula:C₁₂H₁₆N₂O₆*ClH
Molecular Weight:320.73
Hs Code.:

Synonyms:(2S,3R)-1-(2-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)ethylamino)-3-hydroxy-1-oxobutan-2-aminium chloride

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Chemical Property of (2S,3R)-1-(2-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)ethylamino)-3-hydroxy-1-oxobutan-2-aminium chloride

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Technology Process of (2S,3R)-1-(2-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)ethylamino)-3-hydroxy-1-oxobutan-2-aminium chloride

There total 11 articles about (2S,3R)-1-(2-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)ethylamino)-3-hydroxy-1-oxobutan-2-aminium chloride 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: 89.0%

: 1380092-42-1
tert-butyl (2S,3R)-3-tert-butoxy-1-(2-(2,5-dimethoxy-3,6-dioxocyclohexa-1,4-dienyl)ethylamino)-1-oxobutan-2-ylcarbamate

: 1380092-51-2
(2S,3R)-1-(2-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)ethylamino)-3-hydroxy-1-oxobutan-2-aminium chloride

Guidance literature:: With hydrogenchloride; In methanol; at 20 ℃; for 48h;
DOI:10.1016/j.tet.2012.04.024

Reference yield:

: 1380092-14-7
tert-butyl 2-hydroxy-3,5,6-trimethoxyphenethylcarbamate

: 1380092-51-2
(2S,3R)-1-(2-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)ethylamino)-3-hydroxy-1-oxobutan-2-aminium chloride

Guidance literature:: Multi-step reaction with 3 steps

1.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C

1.2: 0 - 20 °C

2.1: [bis(acetoxy)iodo]benzene / water; acetonitrile / 0.25 h / 0 °C

3.1: hydrogenchloride / methanol / 48 h / 20 °C

With hydrogenchloride; [bis(acetoxy)iodo]benzene; trifluoroacetic acid; In methanol; dichloromethane; water; acetonitrile;
DOI:10.1016/j.tet.2012.04.024

Reference yield:

: 4460-86-0,14374-62-0
asaraldehyde

: 1380092-51-2
(2S,3R)-1-(2-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)ethylamino)-3-hydroxy-1-oxobutan-2-aminium chloride

Guidance literature:: Multi-step reaction with 11 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 20 °C

2.1: potassium hydroxide / ethanol / 2 h

3.1: potassium carbonate / acetone / 20 h / Reflux

4.1: 0.5 h / 190 °C / Microwave irradiation; neat (no solvent)

5.1: 1H-imidazole / N,N-dimethyl-formamide / 20 h / 20 °C

6.1: sodium periodate; osmium(VIII) oxide / diethyl ether; water; tert-butyl alcohol / 40 h / 20 °C

7.1: tert-butyldimethylsilane; trifluoroacetic acid / acetonitrile / 18 h / 20 °C

8.1: tetrabutyl ammonium fluoride; triethylamine / tetrahydrofuran / 1 h / 20 °C

9.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C

9.2: 0 - 20 °C

10.1: [bis(acetoxy)iodo]benzene / water; acetonitrile / 0.25 h / 0 °C

11.1: hydrogenchloride / methanol / 48 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium periodate; osmium(VIII) oxide; [bis(acetoxy)iodo]benzene; tert-butyldimethylsilane; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; 1.1: Baeyer-Villiger oxidation / 4.1: Claisen rearrangement / 6.1: Lemieux-Johnson oxidative cleavage;
DOI:10.1016/j.tet.2012.04.024