(+)-(5S,6R)-5-Acetoxy-5,6-dihydro-6-(tosyloxymethyl)-2H-pyran-2-one

Base Information

• Chemical Name: (+)-(5S,6R)-5-Acetoxy-5,6-dihydro-6-(tosyloxymethyl)-2H-pyran-2-one
• CAS No.: 84679-45-8
• Molecular Formula: C₁₅H₁₆O₇S
• Molecular Weight: 340.354
• Mol file: 84679-45-8.mol

Synonyms:(+)-(5S,6R)-5-Acetoxy-5,6-dihydro-6-(tosyloxymethyl)-2H-pyran-2-one

Chemical Property of (+)-(5S,6R)-5-Acetoxy-5,6-dihydro-6-(tosyloxymethyl)-2H-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(5S,6R)-5-Acetoxy-5,6-dihydro-6-(tosyloxymethyl)-2H-pyran-2-one

There total 2 articles about (+)-(5S,6R)-5-Acetoxy-5,6-dihydro-6-(tosyloxymethyl)-2H-pyran-2-one 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: 78.0%

6-O-p-tolylsulfonyl-3,4-di-O-acetyl-D-glucal (18546-25-3) → (+)-(5S,6R)-5-Acetoxy-5,6-dihydro-6-(tosyloxymethyl)-2H-pyran-2-one (84679-45-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; boron trifluoride diethyl etherate; In dichloromethane; for 0.5h; Ambient temperature; addition between -10 deg C and 0 deg C; further oxidants: pyridinium chlorochromate, chromium trioxide;

DOI:10.1016/S0040-4039(00)87705-9

Reference yield:

D-glucose (50-99-7) → (+)-(5S,6R)-5-Acetoxy-5,6-dihydro-6-(tosyloxymethyl)-2H-pyran-2-one (84679-45-8)

Guidance literature:

Multi-step reaction with 2 steps

2: 76 percent / MCPBA/BF₃ / CH₂Cl₂ / 30 h / from -30 deg C to 0 deg C

With boron trifluoride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/S0040-4039(00)95645-4

Reference yield: 90.0%

(+)-(5S,6R)-5-Acetoxy-5,6-dihydro-6-(tosyloxymethyl)-2H-pyran-2-one (84679-45-8) → Toluene-4-sulfonic acid (S)-6-oxo-5,6-dihydro-2H-pyran-2-ylmethyl ester (111860-07-2)

Guidance literature:

With hydrogenchloride; amalgamated zinc; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(00)95645-4

upstream raw materials:

6-O-p-tolylsulfonyl-3,4-di-O-acetyl-D-glucal

D-glucose

Downstream raw materials:

Toluene-4-sulfonic acid (S)-6-oxo-5,6-dihydro-2H-pyran-2-ylmethyl ester

Toluene-4-sulfonic acid (2S,6S)-6-ethoxy-3,6-dihydro-2H-pyran-2-ylmethyl ester

((2S,6S)-6-Ethoxy-3,6-dihydro-2H-pyran-2-ylmethyl)-triphenyl-phosphonium; iodide

6-tosyloxymethyl-5,6-dihydro-2H-pyran-2-one