allyl 4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside

Base Information

• Chemical Name: allyl 4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside
• CAS No.: 527687-46-3
• Molecular Formula: C₃₅H₅₁NO₁₄
• Molecular Weight: 709.788
• Mol file: 527687-46-3.mol

Synonyms:allyl 4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside

Chemical Property of allyl 4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside

There total 6 articles about allyl 4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-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: 75.0%

p-Anisaldehyde dimethyl acetal (2186-92-7) + allyl β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside (527687-44-1) → allyl 4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside (527687-46-3)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 20 ℃; for 15h;

DOI:10.1016/S0008-6215(02)00355-5

Reference yield:

allyl 2-acetamido-2-deoxy-α-D-glucopyranoside (54400-75-8) → allyl 4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside (527687-46-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 85 percent / pyridine / CH₂Cl₂ / 3 h / 0 °C

2.1: pyridine; triflic acid anhydride / CH₂Cl₂ / 2 h / -35 - 0 °C

2.2: 45 percent / NaOH / H₂O / Heating

3.1: 45 percent / BF₃*OEt₂; mol. sieves 4 Angstroem / CH₂Cl₂ / -25 °C

4.1: 97 percent / NaOMe / methanol / 3 h / 20 °C

5.1: 75 percent / pTsOH*H₂O / dimethylformamide / 15 h / 20 °C

With pyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(02)00355-5

Reference yield:

pivaloyl chloride (3282-30-2) → allyl 4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside (527687-46-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 85 percent / pyridine / CH₂Cl₂ / 3 h / 0 °C

2.1: pyridine; triflic acid anhydride / CH₂Cl₂ / 2 h / -35 - 0 °C

2.2: 45 percent / NaOH / H₂O / Heating

3.1: 45 percent / BF₃*OEt₂; mol. sieves 4 Angstroem / CH₂Cl₂ / -25 °C

4.1: 97 percent / NaOMe / methanol / 3 h / 20 °C

5.1: 75 percent / pTsOH*H₂O / dimethylformamide / 15 h / 20 °C

With pyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(02)00355-5

upstream raw materials:

p-Anisaldehyde dimethyl acetal

allyl β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside

allyl 2-acetamido-2-deoxy-α-D-glucopyranoside

pivaloyl chloride

Downstream raw materials:

allyl 3,4-di-O-acetyl-2-O-methyl-β-L-fucopyranosyl-(1-> 2)-3-O-benzoyl-4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside

allyl 3-O-benzoyl-4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside