(2S,3S,4S)-4-[2-(5-benzyloxypyridyl)]-2-hydroxy-3-methyl-butano-4-lactone

Base Information

• Chemical Name: (2S,3S,4S)-4-[2-(5-benzyloxypyridyl)]-2-hydroxy-3-methyl-butano-4-lactone
• CAS No.: 909913-46-8
• Molecular Formula: C₁₇H₁₇NO₄
• Molecular Weight: 299.326
• Mol file: 909913-46-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (2S,3S,4S)-4-[2-(5-benzyloxypyridyl)]-2-hydroxy-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: 74.0%

(3S,4S)-4-(5-Benzyloxy-pyridin-2-yl)-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-butyric acid methyl ester → (2S,3S,4S)-4-[2-(5-benzyloxypyridyl)]-2-hydroxy-3-methyl-butano-4-lactone (909913-46-8) + (2R,3S,4S)-4-[2-(5-benzyloxypyridyl)]-2-hydroxy-3-methyl-butano-4-lactone

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/j.tetasy.2006.06.010

Reference yield:

5-Hydroxy-2-methylpyridine (1121-78-4) → (2S,3S,4S)-4-[2-(5-benzyloxypyridyl)]-2-hydroxy-3-methyl-butano-4-lactone (909913-46-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 91 percent / NaH / dimethylformamide; various solvent(s) / 0 °C

2.1: m-chloroperbenzoic acid / CHCl₃ / 0 - 20 °C

3.1: 95 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

4.1: Zn / benzene / 1.5 h / Heating

5.1: 81 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

6.1: 87 percent / Pseudomonas sp. lipase / diisopropyl ether / 12 h / 33 °C

7.1: 93 percent / imidazole / dimethylformamide / 12 h / 20 °C

8.1: 98 percent / potassium carbonate / methanol / 2 h / 20 °C

9.1: 60 percent / PCC / CH₂Cl₂ / 10 h / 20 °C

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

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

10.3: 66 percent / HgCl₂; HgO / H₂O / 4 h / 20 °C

11.1: 74 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; Pseudomonas sp. lipase; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; di-isopropyl ether; N,N-dimethyl-formamide; benzene; 3.1: Swern oxidation / 4.1: Reformatsky reaction;

DOI:10.1016/j.tetasy.2006.06.010

Reference yield:

5-benzyloxy-2-methyl-pyridine (63793-98-6) → (2S,3S,4S)-4-[2-(5-benzyloxypyridyl)]-2-hydroxy-3-methyl-butano-4-lactone (909913-46-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: m-chloroperbenzoic acid / CHCl₃ / 0 - 20 °C

2.1: 95 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

3.1: Zn / benzene / 1.5 h / Heating

4.1: 81 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

5.1: 87 percent / Pseudomonas sp. lipase / diisopropyl ether / 12 h / 33 °C

6.1: 93 percent / imidazole / dimethylformamide / 12 h / 20 °C

7.1: 98 percent / potassium carbonate / methanol / 2 h / 20 °C

8.1: 60 percent / PCC / CH₂Cl₂ / 10 h / 20 °C

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

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

9.3: 66 percent / HgCl₂; HgO / H₂O / 4 h / 20 °C

10.1: 74 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; Pseudomonas sp. lipase; tetrabutyl ammonium fluoride; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; di-isopropyl ether; N,N-dimethyl-formamide; benzene; 2.1: Swern oxidation / 3.1: Reformatsky reaction;

DOI:10.1016/j.tetasy.2006.06.010

upstream raw materials:

3-(5-benzyloxy-pyridin-2-yl)-2-methyl-3-oxo-propionic acid methyl ester

(2S,3S)-3-[2-(5-benzyloxypyridyl)]-2-methyl-1,3-propanediol

(2S,3S)-1-acetoxy-3-[2-(5-benzyloxypyridyl)]-2-methyl-3-propanol

(2R,3S)-3-[2-(5-benzyloxypyridyl)]-3-tert-butyldimethylsilyloxy-2-methylpropanal

Downstream raw materials:

(2S,3S,4S)-2-amino-4-[2-(5-benzyloxypyridyl)]-3-methyl-butano-4-lactone

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