3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-amino-3-hydroxy-3-(1H-1,2,3-triazol-4-yl)butanoate

Base Information

Chemical Name:3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-amino-3-hydroxy-3-(1H-1,2,3-triazol-4-yl)butanoate
CAS No.:1363374-87-1
Molecular Formula:C₁₁H₂₀N₄O₅
Molecular Weight:288.304
Hs Code.:

Synonyms:3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-amino-3-hydroxy-3-(1H-1,2,3-triazol-4-yl)butanoate

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Chemical Property of 3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-amino-3-hydroxy-3-(1H-1,2,3-triazol-4-yl)butanoate

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Technology Process of 3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-amino-3-hydroxy-3-(1H-1,2,3-triazol-4-yl)butanoate

There total 1 articles about 3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-amino-3-hydroxy-3-(1H-1,2,3-triazol-4-yl)butanoate 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:

: 99314-44-0
(3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate

: 1363374-87-1
3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-amino-3-hydroxy-3-(1H-1,2,3-triazol-4-yl)butanoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: triethylamine; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 36 h / 70 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

2.2: 0.5 h

3.1: dichloromethane / -78 °C / Inert atmosphere

3.2: 2.08 h / -78 °C / Inert atmosphere

3.3: 0.67 h / -78 - 0 °C

4.1: isopropylmagnesium bromide / 2-methyltetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

4.2: 2 h / 20 °C

5.1: dichloromethane / -78 °C / Inert atmosphere

5.2: 2.58 h / -78 °C / Inert atmosphere

5.3: 0.67 h / -78 - 0 °C

6.1: tetrahydrofuran / 0.03 h / -78 °C / Inert atmosphere

6.2: 0.25 h / pH 7

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere

8.1: water; sodium L-ascorbate; copper(II) sulfate / tert-butyl alcohol / 24 h / 20 °C / Inert atmosphere

9.1: hydrogen / palladium 10% on activated carbon / methanol / 1 h

9.2: 18 h

With boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; isopropylmagnesium bromide; tetra-(n-butyl)ammonium iodide; copper(II) sulfate; sodium L-ascorbate; triethylamine; palladium 10% on activated carbon; In tetrahydrofuran; 2-methyltetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

Reference yield: 44.0%

: 728878-27-1
4-[(4'-aminophenyl)buta-1,3-diyn-1-yl]benzoic acid

: 1363374-87-1
3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-amino-3-hydroxy-3-(1H-1,2,3-triazol-4-yl)butanoate

: 1363374-89-3
3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-(4-((4-aminophenyl)buta-1,3-diyn-1-yl)benzamido)-3-hydroxy-3-(1H-1,2,3-triazol-4-yl)butanoate

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 37h; Inert atmosphere;

Reference yield:

: 1363374-87-1
3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-amino-3-hydroxy-3-(1H-1,2,3-triazol-4-yl)butanoate

: 1363368-54-0
4-((4-aminophenyl)buta-1,3-diyn-1-yl)-N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxo-3-(1H-1,2,3-triazol-4-yl)butan-2-yl)benzamide

Guidance literature:: Multi-step reaction with 2 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 19 h / 0 - 20 °C / Inert atmosphere

2: potassium cyanide; hydroxylamine / methanol / 0 - 20 °C / Inert atmosphere

With potassium cyanide; hydroxylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/jm4007774