N-(9-fluorenylmethoxycarbonyl)-O-[2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-L-serine phenacyl ester

Base Information

• Chemical Name: N-(9-fluorenylmethoxycarbonyl)-O-[2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-L-serine phenacyl ester
• CAS No.: 1192142-94-1
• Molecular Formula: C₁₁₀H₁₁₂N₂O₂₂
• Molecular Weight: 1814.1
• Mol file: 1192142-94-1.mol

Synonyms:N-(9-fluorenylmethoxycarbonyl)-O-[2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-L-serine phenacyl ester

Chemical Property of N-(9-fluorenylmethoxycarbonyl)-O-[2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-L-serine phenacyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(9-fluorenylmethoxycarbonyl)-O-[2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-L-serine phenacyl ester

There total 2 articles about N-(9-fluorenylmethoxycarbonyl)-O-[2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-L-serine phenacyl ester 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: 80.0%

2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-D-mannopyranosyl fluoride + N-Fmoc serine phenacyl ester (125760-26-1) → N-(9-fluorenylmethoxycarbonyl)-O-[2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-mannopyranosyl]-L-serine phenacyl ester (1192143-24-0) + N-(9-fluorenylmethoxycarbonyl)-O-[2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-L-serine phenacyl ester (1192142-94-1)

Guidance literature:

With zirconocene dichloride; silver perchlorate; In dichloromethane; at -40 - 0 ℃; for 3h; stereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tet.2009.07.080

Reference yield: 41.0%

phenyl 2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-1-thio-α-D-mannnopyranoside (1192142-81-6) + N-Fmoc serine phenacyl ester (125760-26-1) → N-(9-fluorenylmethoxycarbonyl)-O-[2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-mannopyranosyl]-L-serine phenacyl ester (1192143-24-0) + N-(9-fluorenylmethoxycarbonyl)-O-[2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-L-serine phenacyl ester (1192142-94-1)

Guidance literature:

phenyl 2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-1-thio-α-D-mannnopyranoside; N-Fmoc serine phenacyl ester; With N-iodo-succinimide; In dichloromethane; at -20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With trifluorormethanesulfonic acid; In dichloromethane; at -20 - 0 ℃; for 4.5h; optical yield given as %de; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tet.2009.07.080

Reference yield: 85.0%

N-(9-fluorenylmethoxycarbonyl)-O-[2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-L-serine phenacyl ester (1192142-94-1) → N-(9-fluorenylmethoxycarbonyl)-O-[2,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-L-serine phenacyl ester (1192142-96-3)

Guidance literature:

With water; trifluoroacetic acid; In dichloromethane; at -10 ℃; for 0.5h;

DOI:10.1016/j.tet.2009.07.080

upstream raw materials:

phenyl 2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-1-thio-α-D-mannnopyranoside

N-Fmoc serine phenacyl ester

Downstream raw materials:

N-(9-fluorenylmethoxycarbonyl)-O-[2,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-L-serine phenacyl ester