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

Base Information

• Chemical Name: 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
• CAS No.: 527687-53-2
• Molecular Formula: C₅₃H₇₁NO₂₁
• Molecular Weight: 1058.14
• Mol file: 527687-53-2.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 10 articles about 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 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: 48.0%

S-ethyl 3,4-di-O-acetyl-2-O-methyl-1-thio-β-L-fucopyranoside (418764-38-2) + 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 (527687-48-5) → allyl 3,4-di-O-acetyl-2-O-methyl-α-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 3,4-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 (527687-53-2)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; MS 4 Angstroem; In diethyl ether; dichloromethane; at -20 - 5 ℃;

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

Reference yield:

1-benzoylimidazole (10364-94-0) → 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 (527687-53-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / CHCl₃ / 48 h / 80 °C

2: 20 percent / TfOH; NIS; MS 4 Angstroem / CH₂Cl₂; diethyl ether / -20 - 5 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; MS 4 Angstroem; In diethyl ether; dichloromethane; chloroform;

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

Reference yield:

allyl 2-acetamido-2-deoxy-α-D-glucopyranoside (54400-75-8) → 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 (527687-53-2)

Guidance literature:

Multi-step reaction with 7 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

6.1: 87 percent / CHCl₃ / 48 h / 80 °C

7.1: 20 percent / TfOH; NIS; MS 4 Angstroem / CH₂Cl₂; diethyl ether / -20 - 5 °C

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; trifluoromethylsulfonic anhydride; 4 A molecular sieve; MS 4 Angstroem; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; In methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide;

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

upstream raw materials:

S-ethyl 3,4-di-O-acetyl-2-O-methyl-1-thio-β-L-fucopyranoside

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

1-benzoylimidazole

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