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

Base Information

• Chemical Name: 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
• CAS No.: 856409-88-6
• Molecular Formula: C₅₇H₅₈N₂O₁₂
• Molecular Weight: 963.094
• Mol file: 856409-88-6.mol

Synonyms:

Chemical Property of 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

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-6-O-benzyl-2-deoxy-α-D-glucopyranoside

There total 2 articles about 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 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 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) → 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 (856409-88-6)

Guidance literature:

Multi-step reaction with 2 steps

1: [RhCl(PPh₃)3] / aq. ethanol; toluene / 5 h / Heating

2: 482 mg / HCOOH / aq. ethanol; toluene / 2 h / Heating

With formic acid; tris(triphenylphosphine)rhodium(I) chloride; In ethanol; toluene;

DOI:10.1135/cccc20041781

Reference yield:

N-{(2S,3R,4R,5S,6R)-2-Benzyloxy-6-benzyloxymethyl-5-[(2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-yloxy]-4-[((E)-propenyl)oxy]-tetrahydro-pyran-3-yl}-acetamide → 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 (856409-88-6)

Guidance literature:

With formic acid; In ethanol; toluene; for 2h; Heating;

DOI:10.1135/cccc20041781

Reference yield: 17.0%

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-6-O-benzyl-2-deoxy-α-D-glucopyranoside (856409-88-6) → 1,5-anhydrotri-O-benzyl-2-phthalimido-2-deoxy-D-arabino-hex-1-enitol + 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:

ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-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; With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 1h;

With methyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 36h;

DOI:10.1135/cccc20041781

upstream raw materials:

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