4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: 4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 148437-23-4
• Molecular Formula: C₆₀H₆₁NO₁₅
• Molecular Weight: 1036.14
• Mol file: 148437-23-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester

There total 1 articles about 4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl 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: 74.0%

p-Methoxyphenyl O-(2,4-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (138906-46-4) + levulinic acid (123-76-2) → 4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester (148437-23-4)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; 2-chloro-1-methyl-pyridinium iodide; In 1,2-dichloro-ethane;

DOI:10.1016/S0040-4039(00)77492-2

Reference yield: 98.0%

4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-fluoro-tetrahydro-pyran-3-yloxy]-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl ester (148434-00-8) + 4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester (148437-23-4) → C115H115ClN2O29

Guidance literature:

With Cp₂Hf(OTf)2; In 1,2-dichloro-ethane; at -23 ℃;

DOI:10.1016/S0040-4039(00)77492-2

Reference yield:

4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester (148437-23-4) → 4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6R)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxy-tetrahydro-pyran-3-yloxy]-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl ester (148419-37-8)

Guidance literature:

Multi-step reaction with 2 steps

1: DMAP / pyridine

2: CAN / acetonitrile; toluene; H₂O

With dmap; ammonium cerium(IV) nitrate; In pyridine; water; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)77492-2

upstream raw materials:

p-Methoxyphenyl O-(2,4-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

levulinic acid

Downstream raw materials:

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

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

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