ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3-O-acetyl-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3-O-acetyl-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside
• CAS No.: 133411-36-6
• Molecular Formula: C₆₁H₈₇NO₂₈S₂
• Molecular Weight: 1346.48
• Mol file: 133411-36-6.mol

Synonyms:ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3-O-acetyl-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside

Chemical Property of ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3-O-acetyl-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3-O-acetyl-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside

There total 13 articles about ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3-O-acetyl-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside 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: 94.0%

acetic anhydride (108-24-7) + ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosylonate)-(2->3)-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside (133411-35-5) → ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3-O-acetyl-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside (133411-36-6)

Guidance literature:

With pyridine; at 50 ℃; for 22h;

DOI:10.1016/0008-6215(96)00015-8

Reference yield:

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2) → ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3-O-acetyl-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside (133411-36-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / CH₂Cl₂ / 48 h / 30 °C

2: 72 percent / 1.) 3A molecular sieves, 2.) silver trifluoromethanesulfonate / acetonitrile / 1.) 40 deg C, 14 h, 2.) 60 deg C, 1 d, 3.) 70 deg C, 1 d

3: 94 percent / pyridine / 22 h / 50 °C

With pyridine; 3 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; acetonitrile;

DOI:10.1016/0008-6215(96)00015-8

Reference yield:

pivaloyl chloride (3282-30-2) → ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3-O-acetyl-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside (133411-36-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / 4-dimethylaminopyridine, pyridine / 24 h / 40 °C

2: 88 percent / 4-dimethylaminopyridine, 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 2.5 h / -78 °C

3: 96 percent / p-toluenesulfonic acid monohydrate / methanol / 1.5 h / 50 °C

4: 72 percent / 1.) 3A molecular sieves, 2.) silver trifluoromethanesulfonate / acetonitrile / 1.) 40 deg C, 14 h, 2.) 60 deg C, 1 d, 3.) 70 deg C, 1 d

5: 94 percent / pyridine / 22 h / 50 °C

With pyridine; dmap; 3 A molecular sieve; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/0008-6215(96)00015-8

upstream raw materials:

acetic anhydride

ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosylonate)-(2->3)-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

pivaloyl chloride