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

Base Information

• Chemical Name: benzyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 89067-93-6
• Molecular Formula: C₆₃H₅₈N₂O₁₃
• Molecular Weight: 1051.16
• Mol file: 89067-93-6.mol

Synonyms:benzyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about benzyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-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%

benzyl O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (89067-92-5) → benzyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (89067-93-6)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; at 20 ℃; for 1h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ja307628w

Reference yield:

benzyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside (80035-36-5) + ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (138730-66-2) → benzyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (89067-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.67 h / -20 - 0 °C / Molecular sieve; Inert atmosphere

2: guanidine hydrochloride; sodium methylate / methanol / 2 h / 20 °C / pH 9 / Inert atmosphere

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; guanidine hydrochloride; sodium methylate; In methanol; dichloromethane;

DOI:10.1021/jacs.6b12080

Reference yield:

benzyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside (80035-36-5) → benzyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (89067-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / N-iodosuccinimide; 4 Angstroem molecular sieves; TfOH / CH₂Cl₂ / 1 h / -78 °C

2: 90 percent / aq. H₂O₂; LiOH / tetrahydrofuran / 12 h / 0 °C

With lithium hydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; dihydrogen peroxide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm0489511

upstream raw materials:

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

benzyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside

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

4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose

Downstream raw materials:

benzyl O-(3,6-di-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

C₈₉H₈₈N₂O₁₈

benzyl 2-O-benzyl-3-O-p-methoxybenzyl-4,6-O-(R)-benzylidene-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

benzyl 2-O-benzyl-4,6-O-(R)-benzylidene-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside