2,2-Dimethyl-3-oxo-butyric acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-3-oxo-butyric acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester
• CAS No.: 256351-19-6
• Molecular Formula: C₃₉H₄₂O₇S
• Molecular Weight: 654.824
• Mol file: 256351-19-6.mol

Synonyms:2,2-Dimethyl-3-oxo-butyric acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Chemical Property of 2,2-Dimethyl-3-oxo-butyric acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-3-oxo-butyric acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

There total 1 articles about 2,2-Dimethyl-3-oxo-butyric acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 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:

2-Methyl-3-oxo-butyric acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester (256351-18-5) + methyl iodide (74-88-4) → 2,2-Dimethyl-3-oxo-butyric acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester (256351-19-6)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/ja982414m

Reference yield:

2,2-Dimethyl-3-oxo-butyric acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester (256351-19-6) → 2,2-Dimethyl-3-oxo-butyric acid (2S,3R,4S,5R,6R)-2-benzenesulfinyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -60 - -5 ℃; for 1h; Yield given;

DOI:10.1021/ja982414m

Reference yield:

2,2-Dimethyl-3-oxo-butyric acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester (256351-19-6) → 2,2-Dimethyl-3-oxo-butyric acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yl ester (216668-54-1)

Guidance literature:

Multi-step reaction with 2 steps

1: mCPBA / CH₂Cl₂ / 1 h / -60 - -5 °C

2: 92 percent / Tf₂O, DTBMP / ethyl acetate / 0.08 h / -78 °C

With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; ethyl acetate;

DOI:10.1021/ja982414m

upstream raw materials:

2-Methyl-3-oxo-butyric acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

methyl iodide

Downstream raw materials:

2,2-Dimethyl-3-oxo-butyric acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yl ester