benzyl 4-O-acetyl-2,3-di-O-benzoyl-6-deoxy-6-fluoro-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-mannopyranoside

Base Information

• Chemical Name: benzyl 4-O-acetyl-2,3-di-O-benzoyl-6-deoxy-6-fluoro-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-mannopyranoside
• CAS No.: 417711-25-2
• Molecular Formula: C₅₆H₄₉FO₁₆
• Molecular Weight: 996.994
• Mol file: 417711-25-2.mol

Synonyms:benzyl 4-O-acetyl-2,3-di-O-benzoyl-6-deoxy-6-fluoro-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-mannopyranoside

Chemical Property of benzyl 4-O-acetyl-2,3-di-O-benzoyl-6-deoxy-6-fluoro-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 4-O-acetyl-2,3-di-O-benzoyl-6-deoxy-6-fluoro-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-mannopyranoside

There total 9 articles about benzyl 4-O-acetyl-2,3-di-O-benzoyl-6-deoxy-6-fluoro-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-mannopyranoside 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:

(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol (15548-45-5) → benzyl 4-O-acetyl-2,3-di-O-benzoyl-6-deoxy-6-fluoro-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-mannopyranoside (417711-25-2)

Guidance literature:

Multi-step reaction with 6 steps

1: TsOH*H₂O / acetone

2: H₂O

3: 82 percent / Et₃N / acetonitrile / 0.5 h

4: 88 percent / AgOTf; 2,4,6-collidine / CH₂Cl₂ / 0.5 h

5: pyridinium perchlorate / acetonitrile; H₂O / 4 h / 75 - 80 °C

6: 938 mg / pyridine / 2 h / 20 °C

With pyridine; 2,4,6-trimethyl-pyridine; water; silver trifluoromethanesulfonate; pyridinium perchlorate; toluene-4-sulfonic acid; triethylamine; In dichloromethane; water; acetone; acetonitrile;

Reference yield:

benzyl 2,3-O-isopropylidene-α-D-mannopyranoside (139722-12-6) → benzyl 4-O-acetyl-2,3-di-O-benzoyl-6-deoxy-6-fluoro-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-mannopyranoside (417711-25-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / Et₃N / acetonitrile / 0.5 h

2: 88 percent / AgOTf; 2,4,6-collidine / CH₂Cl₂ / 0.5 h

3: pyridinium perchlorate / acetonitrile; H₂O / 4 h / 75 - 80 °C

4: 938 mg / pyridine / 2 h / 20 °C

With pyridine; 2,4,6-trimethyl-pyridine; silver trifluoromethanesulfonate; pyridinium perchlorate; triethylamine; In dichloromethane; water; acetonitrile;

Reference yield:

methyl 2,3-di-O-benzoyl-6-deoxy-6-fluoro-β-D-galactopyranoside (117124-70-6) → benzyl 4-O-acetyl-2,3-di-O-benzoyl-6-deoxy-6-fluoro-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-mannopyranoside (417711-25-2)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 20 °C

2: 533 mg / H₂SO₄ / 4.5 h / 0 - 20 °C

3: 100 percent / HBr; Ac₂O; AcOH / 4 h / 20 °C

4: 88 percent / AgOTf; 2,4,6-collidine / CH₂Cl₂ / 0.5 h

5: pyridinium perchlorate / acetonitrile; H₂O / 4 h / 75 - 80 °C

6: 938 mg / pyridine / 2 h / 20 °C

With pyridine; 2,4,6-trimethyl-pyridine; sulfuric acid; hydrogen bromide; silver trifluoromethanesulfonate; pyridinium perchlorate; acetic anhydride; acetic acid; In dichloromethane; water; acetonitrile;

upstream raw materials:

(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

benzyl 2,3-O-isopropylidene-α-D-mannopyranoside

benzyl 2,3,4,6-bis(di-O-isopropylidene)-α-D-mannopyranoside

methyl 2,3-di-O-benzoyl-6-deoxy-6-fluoro-β-D-galactopyranoside

Downstream raw materials:

4-O-acetyl-2,3-di-O-benzoyl-6-deoxy-6-fluoro-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-mannopyranose