ethyl 6-O-benzoyl-3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 6-O-benzoyl-3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 860639-92-5
• Molecular Formula: C₃₀H₂₉NO₇S
• Molecular Weight: 547.629
• Mol file: 860639-92-5.mol

Synonyms:ethyl 6-O-benzoyl-3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 6-O-benzoyl-3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 6-O-benzoyl-3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 4 articles about ethyl 6-O-benzoyl-3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 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: 84.0%

benzoyl chloride (98-88-4) + ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-D-glucopyranoside (123212-53-3) → ethyl 6-O-benzoyl-3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (860639-92-5)

Guidance literature:

ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-D-glucopyranoside; With ethylene glycol; trifluoroacetic acid; In dichloromethane; for 1h;

benzoyl chloride; With pyridine; at 0 ℃; for 2h;

DOI:10.1081/CAR-200061584

Reference yield:

Benzoic acid (2R,4R,5R,6S)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-oxo-tetrahydro-pyran-2-ylmethyl ester (860640-08-0) → ethyl 6-O-benzoyl-3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (860639-92-5) + ethyl 6-O-benzoyl-3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

Guidance literature:

With zinc(II) tetrahydroborate; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.5h; Title compound not separated from byproducts;

DOI:10.1081/CAR-200061584

Reference yield:

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside (99409-33-3) → ethyl 6-O-benzoyl-3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (860639-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 84 percent / NaH / dimethylformamide

2.1: ethylene glycol; trifluoroacetic acid / CH₂Cl₂ / 1 h

2.2: 84 percent / pyridine / 2 h / 0 °C

With sodium hydride; ethylene glycol; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1081/CAR-200061584

upstream raw materials:

Benzoic acid (2R,4R,5R,6S)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-oxo-tetrahydro-pyran-2-ylmethyl ester

benzoyl chloride

ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-D-glucopyranoside

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

Downstream raw materials:

Benzoic acid (2R,4R,5R,6S)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-oxo-tetrahydro-pyran-2-ylmethyl ester

Benzoic acid (2R,3S,4R,5R,6S)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-ylmethyl ester