(2R,3R,4R)-2-azido-4-[2-(5-benzyloxypyridyl)]-3-methyl-butano-4-lactone

Base Information

Chemical Name:(2R,3R,4R)-2-azido-4-[2-(5-benzyloxypyridyl)]-3-methyl-butano-4-lactone
CAS No.:909913-34-4
Molecular Formula:C₁₇H₁₆N₄O₃
Molecular Weight:324.339
Hs Code.:

Synonyms:(2R,3R,4R)-2-azido-4-[2-(5-benzyloxypyridyl)]-3-methyl-butano-4-lactone

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Chemical Property of (2R,3R,4R)-2-azido-4-[2-(5-benzyloxypyridyl)]-3-methyl-butano-4-lactone

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Technology Process of (2R,3R,4R)-2-azido-4-[2-(5-benzyloxypyridyl)]-3-methyl-butano-4-lactone

There total 6 articles about (2R,3R,4R)-2-azido-4-[2-(5-benzyloxypyridyl)]-3-methyl-butano-4-lactone 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: 58.0%

: 909913-32-2
(2R,3R,4R)-4-[2-(5-benzyloxypyridyl)]-2-hydroxy-3-methyl-butano-4-lactone

: (4R)-4-[2-(5-benzyloxypyridyl)]-3-methyl-2-buteno-4-lactone

: (2S,3R,4R)-2-azido-4-[2-(5-benzyloxypyridyl)]-3-methyl-butano-4-lactone

: 909913-34-4
(2R,3R,4R)-2-azido-4-[2-(5-benzyloxypyridyl)]-3-methyl-butano-4-lactone

Guidance literature:: (2R,3R,4R)-4-[2-(5-benzyloxypyridyl)]-2-hydroxy-3-methyl-butano-4-lactone; With 1H-imidazole; iodine; triphenylphosphine; In tetrahydrofuran; at 0 ℃;

With sodium azide; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1016/j.tetasy.2006.06.010

Reference yield:

: 909913-42-4
(2R,3R)-1-acetoxy-3-[2-(5-benzyloxypyridyl)]-2-methyl-3-propanol

: 909913-34-4
(2R,3R,4R)-2-azido-4-[2-(5-benzyloxypyridyl)]-3-methyl-butano-4-lactone

Guidance literature:: Multi-step reaction with 6 steps

1.1: 97 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: 92 percent / potassium carbonate / methanol / 2 h / 20 °C

3.1: 42 percent / PCC / CH₂Cl₂ / 10 h / 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 1.33 h / -78 - -20 °C

4.2: tetrahydrofuran; hexane / 4 h / -78 - 0 °C

4.3: 72 percent / HgCl₂; HgO / H₂O / 4 h / 20 °C

5.1: 74 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

6.1: triphenylphosphine; imidazole; iodine / tetrahydrofuran / 0 °C

6.2: 58 percent / sodium azide / dimethylformamide; tetrahydrofuran / 1 h / 20 °C

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; iodine; potassium carbonate; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2006.06.010

Reference yield:

: 909913-30-0
(2S,3R)-3-[2-(5-benzyloxypyridyl)]-3-tert-butyldimethylsilyloxy-2-methylpropanal

: 909913-34-4
(2R,3R,4R)-2-azido-4-[2-(5-benzyloxypyridyl)]-3-methyl-butano-4-lactone

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1.33 h / -78 - -20 °C

1.2: tetrahydrofuran; hexane / 4 h / -78 - 0 °C

1.3: 72 percent / HgCl₂; HgO / H₂O / 4 h / 20 °C

2.1: 74 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

3.1: triphenylphosphine; imidazole; iodine / tetrahydrofuran / 0 °C

3.2: 58 percent / sodium azide / dimethylformamide; tetrahydrofuran / 1 h / 20 °C

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; iodine; triphenylphosphine; In tetrahydrofuran; hexane;
DOI:10.1016/j.tetasy.2006.06.010