4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-2-benzyloxymethyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: 4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-2-benzyloxymethyl-tetrahydro-pyran-4-yl ester
• CAS No.: 177358-15-5
• Molecular Formula: C₅₇H₆₁NO₁₄S
• Molecular Weight: 1016.18
• Mol file: 177358-15-5.mol

Synonyms:4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-2-benzyloxymethyl-tetrahydro-pyran-4-yl ester

Chemical Property of 4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-2-benzyloxymethyl-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,3S,4S,5R,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-2-benzyloxymethyl-tetrahydro-pyran-4-yl ester

There total 9 articles about 4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-2-benzyloxymethyl-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: 99.0%

levulinic acid (123-76-2) + ethyl 4-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (177358-23-5) → 4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-2-benzyloxymethyl-tetrahydro-pyran-4-yl ester (177358-15-5)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1016/0040-4020(96)00225-6

Reference yield:

benzyl bromide (100-39-0) → 4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-2-benzyloxymethyl-tetrahydro-pyran-4-yl ester (177358-15-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 6 h

2: 100 percent / 70percent acetic acid / 3 h / 60 °C

3: 1.) p-toluenesulfonic acid monohydrate, 2.) 80percent acetic acid / 1.) acetonitrile, 10 min, 2.) acetonitrile, 15 min

4: 99 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 4-dimethylaminopyridine / CH₂Cl₂ / 1.5 h / 0 °C

With dmap; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4020(96)00225-6

Reference yield:

phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-β-D-galactopyranoside (154618-72-1) → 4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-2-benzyloxymethyl-tetrahydro-pyran-4-yl ester (177358-15-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / K₂CO₃, molecular sieves 4A, silver triflate / CH₂Cl₂ / 3.5 h / Ambient temperature

2: 100 percent / K₂CO₃ / dioxane; methanol / 4 h / 0 °C

3: 79 percent / camphorsulfonic acid / 16 h

4: 82 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 6 h

5: 100 percent / 70percent acetic acid / 3 h / 60 °C

6: 1.) p-toluenesulfonic acid monohydrate, 2.) 80percent acetic acid / 1.) acetonitrile, 10 min, 2.) acetonitrile, 15 min

7: 99 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 4-dimethylaminopyridine / CH₂Cl₂ / 1.5 h / 0 °C

With dmap; 4 A molecular sieve; camphor-10-sulfonic acid; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1016/0040-4020(96)00225-6

upstream raw materials:

levulinic acid

ethyl 4-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

benzyl bromide

phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-β-D-galactopyranoside