benzyl N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-L-threonyl-L-threoninate

Base Information

• Chemical Name: benzyl N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-L-threonyl-L-threoninate
• CAS No.: 86117-95-5
• Molecular Formula: C₅₇H₆₂N₂O₁₂
• Molecular Weight: 967.125
• Mol file: 86117-95-5.mol

Synonyms:

Chemical Property of benzyl N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-L-threonyl-L-threoninate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-L-threonyl-L-threoninate

There total 3 articles about benzyl N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-L-threonyl-L-threoninate 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:

2,3,4,6-tetra-O-benzyl-D-galactopyranose (6386-24-9) → benzyl N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-L-threonyl-L-threoninate (86117-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 33 percent / trifluoromethanesulfonic anhydride / acetonitrile; CH₂Cl₂ / 0.25 h / -15 °C

2: 1.) triethylamine, 2.) 1-hydroxybenzotriazole / 1.) THF, 30 min, 0 deg C; 18 h, room temp., 2.) 6 h

With benzotriazol-1-ol; trifluoromethanesulfonic acid anhydride; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1021/jo00163a027

Reference yield:

ester O-nitrophenylique de la N-(benzyloxycarbonyl)-L-threonine (62087-89-2) → benzyl N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-L-threonyl-L-threoninate (86117-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 33 percent / trifluoromethanesulfonic anhydride / acetonitrile; CH₂Cl₂ / 0.25 h / -15 °C

2: 1.) triethylamine, 2.) 1-hydroxybenzotriazole / 1.) THF, 30 min, 0 deg C; 18 h, room temp., 2.) 6 h

With benzotriazol-1-ol; trifluoromethanesulfonic acid anhydride; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1021/jo00163a027

Reference yield:

(2S,3R)-threonine benzyl ester (33640-67-4) + o-nitrophenyl N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-L-threoninate (86117-93-3) → benzyl N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-L-threonyl-L-threoninate (86117-95-5)

Guidance literature:

With benzotriazol-1-ol; triethylamine; Yield given. Multistep reaction; 1.) THF, 30 min, 0 deg C; 18 h, room temp., 2.) 6 h;

DOI:10.1021/jo00163a027

upstream raw materials:

(2S,3R)-threonine benzyl ester

o-nitrophenyl N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-L-threoninate

2,3,4,6-tetra-O-benzyl-D-galactopyranose

ester O-nitrophenylique de la N-(benzyloxycarbonyl)-L-threonine