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

Base Information

• Chemical Name: 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride
• CAS No.: 159734-72-2
• Molecular Formula: C₃₀H₂₈FNO₇
• Molecular Weight: 533.553
• Mol file: 159734-72-2.mol

Synonyms:4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride

Chemical Property of 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride

There total 2 articles about 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride 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: 93.0%

ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (138730-66-2) → 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride (159734-72-2)

Guidance literature:

With pyridine; N-Bromosuccinimide; hydrogen fluoride; In dichloromethane; at 0 ℃;

Reference yield:

ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-35-2) → 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride (159734-72-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / pyridine / 20 h / 20 °C

2: 92.7 percent / NBS; HF/pyridine / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; N-Bromosuccinimide; hydrogen fluoride; In dichloromethane;

DOI:10.1002/chem.200390156

Reference yield: 91.3%

4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride (159734-72-2) → 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (161315-65-7)

Guidance literature:

With trimethylsilylazide; boron trifluoride diethyl etherate; In dichloromethane;

upstream raw materials:

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

ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

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-glucopyranosyl azide

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

acetic acid 4-benzyloxy-2-benzyloxymethyl-6-[4,6-bis-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-phenoxymethyl)-tetrahydro-pyran-3-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester

3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide