[N-(tert-butoxycarbonyl)-O-(2,3,5-tri-O-benzyl-α-L-fucofuranosyl)-D-seryl]-L-glutamic acid 1-methylamide 5-benzyl ester

Base Information

• Chemical Name: [N-(tert-butoxycarbonyl)-O-(2,3,5-tri-O-benzyl-α-L-fucofuranosyl)-D-seryl]-L-glutamic acid 1-methylamide 5-benzyl ester
• CAS No.: 190587-03-2
• Molecular Formula: C₄₈H₅₉N₃O₁₁
• Molecular Weight: 854.01
• Mol file: 190587-03-2.mol

Synonyms:[N-(tert-butoxycarbonyl)-O-(2,3,5-tri-O-benzyl-α-L-fucofuranosyl)-D-seryl]-L-glutamic acid 1-methylamide 5-benzyl ester

Chemical Property of [N-(tert-butoxycarbonyl)-O-(2,3,5-tri-O-benzyl-α-L-fucofuranosyl)-D-seryl]-L-glutamic acid 1-methylamide 5-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [N-(tert-butoxycarbonyl)-O-(2,3,5-tri-O-benzyl-α-L-fucofuranosyl)-D-seryl]-L-glutamic acid 1-methylamide 5-benzyl ester

There total 2 articles about [N-(tert-butoxycarbonyl)-O-(2,3,5-tri-O-benzyl-α-L-fucofuranosyl)-D-seryl]-L-glutamic acid 1-methylamide 5-benzyl 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: 20.5%

N-tert-butoxycarbonyl-D-seryl-L-glutamic acid 1-methylamide 5-benzyl ester (190586-78-8) + 2,3,5-tri-O-benzyl-L-fucofuranosyl fluoride → [N-(tert-butoxycarbonyl)-O-(2,3,5-tri-O-benzyl-α-L-fucofuranosyl)-D-seryl]-L-glutamic acid 1-methylamide 5-benzyl ester (190587-03-2)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; tetramethylurea; tin(ll) chloride; In dichloromethane; at -50 - 20 ℃; for 20h;

DOI:10.1021/jm9707481

Reference yield:

(S)-4-Amino-4-methylcarbamoyl-butyric acid benzyl ester (82594-35-2) → [N-(tert-butoxycarbonyl)-O-(2,3,5-tri-O-benzyl-α-L-fucofuranosyl)-D-seryl]-L-glutamic acid 1-methylamide 5-benzyl ester (190587-03-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 4N HCl in dioxane, 2.) Et₃N, 3.) WSC, HOBt

2: 20.5 percent / 4A molecular sieves, AgOTf, SnCl₂, TMU / CH₂Cl₂ / 20 h / -50 - 20 °C

With hydrogenchloride; 4 A molecular sieve; silver trifluoromethanesulfonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; tetramethylurea; tin(ll) chloride; In dichloromethane;

DOI:10.1021/jm9707481

Reference yield:

[N-(tert-butoxycarbonyl)-O-(2,3,5-tri-O-benzyl-α-L-fucofuranosyl)-D-seryl]-L-glutamic acid 1-methylamide 5-benzyl ester (190587-03-2) → (S)-4-{(R)-2-Amino-3-[(2R,3S,4R,5R)-3,4-bis-benzyloxy-5-((S)-1-benzyloxy-ethyl)-tetrahydro-furan-2-yloxy]-propionylamino}-4-methylcarbamoyl-butyric acid benzyl ester (190587-21-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1021/jm9707481

upstream raw materials:

N-tert-butoxycarbonyl-D-seryl-L-glutamic acid 1-methylamide 5-benzyl ester

(S)-4-Amino-4-methylcarbamoyl-butyric acid benzyl ester

Downstream raw materials:

(S)-4-{(R)-2-Amino-3-[(2R,3S,4R,5R)-3,4-bis-benzyloxy-5-((S)-1-benzyloxy-ethyl)-tetrahydro-furan-2-yloxy]-propionylamino}-4-methylcarbamoyl-butyric acid benzyl ester

[N-(2-tetradecylhexadecanoyl)-O-(2,3,5-tri-O-benzyl-α-L-fucofuranosyl)-D-seryl]-L-glutamic acid 1-methylamide 5-benzyl ester