N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-serine allyl ester

Base Information

• Chemical Name: N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-serine allyl ester
• CAS No.: 184093-93-4
• Molecular Formula: C₆₈H₆₈N₄O₁₄
• Molecular Weight: 1165.31
• Mol file: 184093-93-4.mol

Synonyms:N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-serine allyl ester

Chemical Property of N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-serine allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-serine allyl ester

There total 2 articles about N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-serine allyl 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: 67.0%

phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (74801-29-9) + allyl N-(9-fluorenylmethoxycarbonyl)-[O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1[*]3)]-L-serine (155177-85-8) → N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-serine allyl ester (894392-00-8) + N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-serine allyl ester (184093-93-4)

Guidance literature:

phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside; allyl N-(9-fluorenylmethoxycarbonyl)-[O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1[*]3)]-L-serine; With 4 A molecular sieve; sulfobromophthalein sodium; In various solvent(s); at -78 ℃; for 0.166667h;

With trifluoromethylsulfonic anhydride; In various solvent(s); at -78 ℃; for 0.5h; Further stages.;

DOI:10.1016/j.tet.2008.01.029

Reference yield: 62.0%

2,3,4,6-tetra-O-benzyl-D-galactopyranosyl fluoride (143615-35-4) + allyl N-(9-fluorenylmethoxycarbonyl)-[O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1[*]3)]-L-serine (155177-85-8) → N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-serine allyl ester (894392-00-8) + N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-serine allyl ester (184093-93-4)

Guidance literature:

With 4 A molecular sieve; silver perchlorate; zirconocene dichloride; In dichloromethane; at -15 - 20 ℃; for 16h;

DOI:10.1271/bbb.69.1575

Reference yield: 74.0%

N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-serine allyl ester (184093-93-4) → N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-2-deoxy-α-D-galactopyranosyl]-L-serine allyl ester

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at -15 ℃; for 1h;

DOI:10.1016/j.tet.2003.08.047

upstream raw materials:

2,3,4,6-tetra-O-benzyl-D-galactopyranosyl fluoride

allyl N-(9-fluorenylmethoxycarbonyl)-[O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1[*]3)]-L-serine

phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside