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

Base Information

• Chemical Name: (2R,3S)-3-[2-(5-benzyloxypyridyl)]-3-tert-butyldimethylsilyloxy-2-methylpropanal
• CAS No.: 909913-43-5
• Molecular Formula: C₂₂H₃₁NO₃Si
• Molecular Weight: 385.579
• Mol file: 909913-43-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about (2R,3S)-3-[2-(5-benzyloxypyridyl)]-3-tert-butyldimethylsilyloxy-2-methylpropanal 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: 60.0%

(2S,3S)-3-[2-(5-benzyloxypyridyl)]-3-tert-butyldimethylsilyloxy-2-methyl-1-propanol (909913-45-7) → (2R,3S)-3-[2-(5-benzyloxypyridyl)]-3-tert-butyldimethylsilyloxy-2-methylpropanal (909913-43-5)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 10h;

DOI:10.1016/j.tetasy.2006.06.010

Reference yield:

5-Hydroxy-2-methylpyridine (1121-78-4) → (2R,3S)-3-[2-(5-benzyloxypyridyl)]-3-tert-butyldimethylsilyloxy-2-methylpropanal (909913-43-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 91 percent / NaH / dimethylformamide; various solvent(s) / 0 °C

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

3: 95 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

4: Zn / benzene / 1.5 h / Heating

5: 81 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

6: 87 percent / Pseudomonas sp. lipase / diisopropyl ether / 12 h / 33 °C

7: 93 percent / imidazole / dimethylformamide / 12 h / 20 °C

8: 98 percent / potassium carbonate / methanol / 2 h / 20 °C

9: 60 percent / PCC / CH₂Cl₂ / 10 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; Pseudomonas sp. lipase; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; zinc; In tetrahydrofuran; methanol; dichloromethane; chloroform; di-isopropyl ether; N,N-dimethyl-formamide; benzene; 3: Swern oxidation / 4: Reformatsky reaction;

DOI:10.1016/j.tetasy.2006.06.010

Reference yield:

5-benzyloxy-2-methyl-pyridine (63793-98-6) → (2R,3S)-3-[2-(5-benzyloxypyridyl)]-3-tert-butyldimethylsilyloxy-2-methylpropanal (909913-43-5)

Guidance literature:

Multi-step reaction with 9 steps

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

2: 95 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

3: Zn / benzene / 1.5 h / Heating

4: 81 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

5: 87 percent / Pseudomonas sp. lipase / diisopropyl ether / 12 h / 33 °C

6: 93 percent / imidazole / dimethylformamide / 12 h / 20 °C

7: 98 percent / potassium carbonate / methanol / 2 h / 20 °C

8: 60 percent / PCC / CH₂Cl₂ / 10 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; Pseudomonas sp. lipase; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; zinc; In tetrahydrofuran; methanol; dichloromethane; chloroform; di-isopropyl ether; N,N-dimethyl-formamide; benzene; 2: Swern oxidation / 3: Reformatsky reaction;

DOI:10.1016/j.tetasy.2006.06.010

upstream raw materials:

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

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

Downstream raw materials:

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

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

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