Benzoic acid (2R,3S,4R,5R,6S)-2-(2,2-dimethyl-propionyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-hydroxy-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4R,5R,6S)-2-(2,2-dimethyl-propionyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-hydroxy-tetrahydro-pyran-4-yl ester
• CAS No.: 210472-26-7
• Molecular Formula: C₂₈H₃₁NO₈S
• Molecular Weight: 541.622
• Mol file: 210472-26-7.mol

Synonyms:

Chemical Property of Benzoic acid (2R,3S,4R,5R,6S)-2-(2,2-dimethyl-propionyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-hydroxy-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,4R,5R,6S)-2-(2,2-dimethyl-propionyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-hydroxy-tetrahydro-pyran-4-yl ester

There total 1 articles about Benzoic acid (2R,3S,4R,5R,6S)-2-(2,2-dimethyl-propionyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-hydroxy-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:

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside (99409-33-3) + pivaloyl chloride (3282-30-2) + benzoyl chloride (98-88-4) → Benzoic acid (2R,3S,4R,5R,6S)-2-(2,2-dimethyl-propionyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-hydroxy-tetrahydro-pyran-4-yl ester (210472-26-7)

Guidance literature:

Yield given. Multistep reaction; 1.) pyridine, RT, 30 min; 2.) 60percent AcOH, 100 deg C, 1 h; 3.) 0 deg C, 2 h, pyridine;

DOI:10.1016/S0008-6215(97)10093-3

Reference yield:

Benzoic acid (2R,3S,4R,5R,6S)-2-(2,2-dimethyl-propionyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-hydroxy-tetrahydro-pyran-4-yl ester (210472-26-7) → Benzoic acid (2S,3R,4S,6S)-6-(2,2-dimethyl-propionyloxymethyl)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-ethylsulfanyl-tetrahydro-pyran-4-yl ester (210472-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Tf₂O; 2.) NaI / 1.) CH₂Cl₂, RT, 30 min, pyridine; 2.) dimethoxyethane, RT, 12 h

2: 87 percent / AIBN, tri-n-butyltin hydride / toluene / 2.5 h / Heating

With 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; tri-n-butyl-tin hydride; sodium iodide; In toluene;

DOI:10.1016/S0008-6215(97)10093-3

Reference yield:

Benzoic acid (2R,3S,4R,5R,6S)-2-(2,2-dimethyl-propionyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-hydroxy-tetrahydro-pyran-4-yl ester (210472-26-7) → Benzoic acid (2R,3R,4R,5R,6S)-2-(2,2-dimethyl-propionyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-iodo-tetrahydro-pyran-4-yl ester (210472-27-8)

Guidance literature:

With trifluoromethylsulfonic anhydride; sodium iodide; Yield given. Multistep reaction; 1.) CH₂Cl₂, RT, 30 min, pyridine; 2.) dimethoxyethane, RT, 12 h;

DOI:10.1016/S0008-6215(97)10093-3

upstream raw materials:

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside

pivaloyl chloride

benzoyl chloride

Downstream raw materials:

Benzoic acid (2R,3R,4R,5R,6S)-2-(2,2-dimethyl-propionyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-iodo-tetrahydro-pyran-4-yl ester

Benzoic acid (2S,3R,4S,6S)-6-(2,2-dimethyl-propionyloxymethyl)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-ethylsulfanyl-tetrahydro-pyran-4-yl ester