Phenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside

Base Information

• Chemical Name: Phenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside
• CAS No.: 79528-51-1
• Molecular Formula: C27H23NO6S
• Molecular Weight: 489.549
• Mol file: 79528-51-1.mol

Synonyms:Phenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside

Chemical Property of Phenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Phenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside

There total 8 articles about Phenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-beta-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: 90.0%

benzaldehyde dimethyl acetal (1125-88-8) + 2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione (136882-36-5,79528-50-0) → phenyl 4,6-benzylidene-2-deoxy-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (79528-51-1)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In acetonitrile; at 20 ℃; regioselective reaction; Inert atmosphere; Sonication;

DOI:10.1002/adsc.201100228

Reference yield: 65.0%

benzaldehyde dimethyl acetal (1125-88-8) + phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (79528-49-7) → phenyl 4,6-benzylidene-2-deoxy-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (79528-51-1)

Guidance literature:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside; With sodium methylate; In methanol; at 20 ℃; for 72h;

benzaldehyde dimethyl acetal; With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 70 ℃;

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → phenyl 4,6-benzylidene-2-deoxy-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (79528-51-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 69.5 percent / trimethylsilyl triflate / CH₂Cl₂ / 72 h / Ambient temperature

2: 1.) NaOCH₃; 2.) 4-toluenesulfonic acid monohydrate / 1.) methanol, r.t., 3 h; 2.) r.t., 16 h

With trimethylsilyl trifluoromethanesulfonate; p-toluenesulfonic acid monohydrate; sodium methylate; In dichloromethane;

DOI:10.1016/0008-6215(92)84057-Y

upstream raw materials:

benzaldehyde dimethyl acetal

2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

Downstream raw materials:

phenyl 4,6-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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

phenyl 6-O-acetyl-3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

phenyl 3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside