phenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-pivaloyl-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-pivaloyl-β-D-galactopyranoside
• CAS No.: 865096-60-2
• Molecular Formula: C₂₆H₃₁NO₇
• Molecular Weight: 469.535
• Mol file: 865096-60-2.mol

Synonyms:phenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-pivaloyl-β-D-galactopyranoside

Chemical Property of phenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-pivaloyl-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-pivaloyl-β-D-galactopyranoside

There total 6 articles about phenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-pivaloyl-β-D-galactopyranoside 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: 66.0%

phenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside (865096-57-7) + pivaloyl chloride (3282-30-2) → phenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-pivaloyl-β-D-galactopyranoside (865096-60-2)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1016/j.carres.2005.06.010

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → phenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-pivaloyl-β-D-galactopyranoside (865096-60-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: D-camphor-10-sulfonic acid / dimethylformamide / 31.5 h / 40 °C

1.2: 51 percent / NaHCO₃ / H₂O; CHCl₃

2.1: 66 percent / pyridine / CH₂Cl₂ / 15 h / 20 °C

With pyridine; camphor-10-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2005.06.010

Reference yield:

(3R,4R,5R,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate (76375-60-5) → phenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-pivaloyl-β-D-galactopyranoside (865096-60-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1.8 percent / ZnCl₂; CaSO₄ / 1,2-dichloro-ethane / 18 h / Heating

2.1: 88 percent / NaOMe / methanol / 1 h / 20 °C

3.1: D-camphor-10-sulfonic acid / dimethylformamide / 31.5 h / 40 °C

3.2: 51 percent / NaHCO₃ / H₂O; CHCl₃

4.1: 66 percent / pyridine / CH₂Cl₂ / 15 h / 20 °C

With pyridine; calcium sulfate; camphor-10-sulfonic acid; sodium methylate; zinc(II) chloride; In methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2005.06.010

upstream raw materials:

phenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

pivaloyl chloride

benzaldehyde dimethyl acetal

(3R,4R,5R,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate

Downstream raw materials:

phenyl 2-acetamido-2-deoxy-3-O-pivaloyl-β-D-galactopyranoside