phenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 127061-09-0
• Molecular Formula: C₂₇H₂₃NO₆S
• Molecular Weight: 489.549
• Mol file: 127061-09-0.mol

Synonyms:phenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 4,6-di-O-benzylidene-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 phenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 7 articles about phenyl 4,6-di-O-benzylidene-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: 91.0%

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-di-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (127061-09-0)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; Inert atmosphere;

DOI:10.1002/anie.201101055

Reference yield:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (79528-49-7) → phenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (127061-09-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / MeONa / methanol / 3 h / 20 °C

2: 86 percent / p-TsOH / acetonitrile / 2 h / 20 °C

With sodium methylate; toluene-4-sulfonic acid; In methanol; acetonitrile;

DOI:10.1016/S0957-4166(02)00480-9

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → phenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (127061-09-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / boron trifluoride etherate / CH₂Cl₂

2: 100 percent / MeONa / methanol / 3 h / 20 °C

3: 86 percent / p-TsOH / acetonitrile / 2 h / 20 °C

With boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0957-4166(02)00480-9

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

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

thiophenol

Downstream raw materials:

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

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

3-bromopropanyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

3-thioacetylpropanyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside