p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 1093115-83-3
• Molecular Formula: C₄₂H₃₉NO₆S
• Molecular Weight: 685.841
• Mol file: 1093115-83-3.mol

Synonyms:p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of p-methylphenyl 3,4,6-tri-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 p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 2 articles about p-methylphenyl 3,4,6-tri-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:

benzyl bromide (100-39-0) + p-methylphenyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (220645-79-4) → p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (1093115-83-3)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃;

DOI:10.1016/j.carres.2008.08.024

Reference yield:

p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (172847-90-4) → p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (1093115-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium methylate / methanol / 3 h / 20 °C

1.2: acid resin IR-120

2.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 8 h / 0 - 20 °C / Inert atmosphere

With sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2018.08.039

Reference yield: 88.0%

p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (1093115-83-3) + dibutyl phosphate (107-66-4) → dibutyl-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside phosphate

Guidance literature:

p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside; In dichloromethane; at 20 ℃; for 1h; Molecular sieve; Inert atmosphere;

dibutyl phosphate; With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -40 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tet.2018.08.039

upstream raw materials:

benzyl bromide

p-methylphenyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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

Downstream raw materials:

O-(-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

2-((3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-3-yl)-isoindole-1,3-dione