benzyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: benzyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside
• CAS No.: 210645-13-9
• Molecular Formula: C₆₀H₆₂N₂O₁₂
• Molecular Weight: 1003.16
• Mol file: 210645-13-9.mol

Synonyms:

Chemical Property of benzyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside

There total 9 articles about benzyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-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: 72.0%

benzyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside (60920-82-3) + 2-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl)-isoindole-1,3-dione (210645-10-6) → benzyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside (210645-13-9)

Guidance literature:

With silver trifluoromethanesulfonate; In dichloromethane; 1.) -45 deg C, 1 h, 2.) -20 deg C, 30 min;

DOI:10.1135/cccc19980577

Reference yield: 21.0%

benzyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside (60920-82-3) + ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (168644-99-3) → benzyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside (210645-13-9)

Guidance literature:

With 4 A molecular sieve; methyl trifluoromethanesulfonate; In dichloromethane; at -15 ℃; for 72h;

DOI:10.1135/cccc19980577

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → benzyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside (210645-13-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 72 percent / 4 Angstroem molecular sieves, TiCl₄ / CH₂Cl₂ / 1 h / Ambient temperature

2: 90 percent / CH₃ONa / methanol / 1.) r.t., 2 h, 2.) 3 deg C, overnight

3: 72 percent / NaH / dimethylformamide / Ambient temperature

4: 21 percent / 4 Angstroem molecular sieves, methyl triflate / CH₂Cl₂ / 72 h / -15 °C

With 4 A molecular sieve; sodium methylate; titanium tetrachloride; sodium hydride; methyl trifluoromethanesulfonate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1135/cccc19980577

upstream raw materials:

benzyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside

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

ethyl 3,4,6-tri-O-benzyl-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:

benzyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside

benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside

benzyl 2-acetamido-3-O-allyl-6-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-stearoylamino-β-D-glucopyranosyl)-2-deoxy-α-D-glucopyranoside

benzyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-2-deoxy-α-D-glucopyranoside