4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-3-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-3-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester
• CAS No.: 220775-04-2
• Molecular Formula: C₁₈H₂₄O₇S
• Molecular Weight: 384.45
• Mol file: 220775-04-2.mol

Synonyms:4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-3-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester

Chemical Property of 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-3-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-3-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester

There total 2 articles about 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-3-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-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: 70.0%

levulinic acid (123-76-2) + 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-4-yl ester (220775-00-8) → 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-3-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester (220775-04-2) + phenyl 2-O-TBDMS-3-O-levulinoyl-4-C-methyl-1-thio-β-D-glucopyranoside

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In acetonitrile; at 90 ℃; for 4h; Heating;

DOI:10.1016/S0040-4039(98)80003-8

Reference yield:

(2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol (220774-98-1) → 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-3-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester (220775-04-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / DCC, DMAP / CH₂Cl₂ / 24 h / Heating

2: 70 percent / H₂O, DDQ / acetonitrile / 4 h / 90 °C / Heating

With dmap; water; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(98)80003-8

Reference yield: 65.0%

4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-3-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester (220775-04-2) → phenyl 2-O-levulinoyl-4-C-methyl-1-thio-β-D-glucopyranosiduronic acid

Guidance literature:

With Jones-reagent; In acetone; at 30 ℃; for 1h; sonication;

DOI:10.1016/S0040-4039(98)80003-8

upstream raw materials:

levulinic acid

4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-4-yl ester

(2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol