3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide

Base Information

• Chemical Name: 3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide
• CAS No.: 142545-55-9
• Molecular Formula: C₃₅H₂₆BrNO₉
• Molecular Weight: 684.497
• Mol file: 142545-55-9.mol

Synonyms:3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide

Chemical Property of 3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide

There total 2 articles about 3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide 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:

1,3,4,6-tetra-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranose (142545-54-8) → 3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (142545-55-9)

Guidance literature:

With hydrogen bromide; acetic acid; In dichloromethane; for 2h; Yield given; Ambient temperature;

DOI:10.1016/0008-6215(92)84133-D

Reference yield:

1,3,4,6-tetra-O-benzoyl-2-(2-benzoyloxycarbonylbenzamido)-2-deoxy-β-D-glucopyranose (142545-64-0) → 3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (142545-55-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / Ac₂O / pyridine / 25 h / Heating

2: 48percent HBr, HOAc / CH₂Cl₂ / 2 h / Ambient temperature

With hydrogen bromide; acetic anhydride; acetic acid; In pyridine; dichloromethane;

DOI:10.1016/0008-6215(92)84133-D

Reference yield: 77.0%

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + 3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (142545-55-9) → methyl O-(3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (1233488-75-9)

Guidance literature:

With N-iodo-succinimide; camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/ejoc.201600545

upstream raw materials:

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

1,3,4,6-tetra-O-benzoyl-2-(2-benzoyloxycarbonylbenzamido)-2-deoxy-β-D-glucopyranose

Downstream raw materials:

allyl 3-O-(3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

allyl 3-O-(3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside

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