γ-benzyl N²-tert-butyloxycarbonyl-N³-[1-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)-hexyl-6-amino]-L-glutamate-α-amide

Base Information

• Chemical Name: γ-benzyl N²-tert-butyloxycarbonyl-N³-[1-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)-hexyl-6-amino]-L-glutamate-α-amide
• CAS No.: 167016-50-4
• Molecular Formula: C₅₀H₆₄N₂O₁₀
• Molecular Weight: 853.066
• Mol file: 167016-50-4.mol

Synonyms:γ-benzyl N²-tert-butyloxycarbonyl-N³-[1-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)-hexyl-6-amino]-L-glutamate-α-amide

Chemical Property of γ-benzyl N²-tert-butyloxycarbonyl-N³-[1-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)-hexyl-6-amino]-L-glutamate-α-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of γ-benzyl N²-tert-butyloxycarbonyl-N³-[1-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)-hexyl-6-amino]-L-glutamate-α-amide

There total 1 articles about γ-benzyl N²-tert-butyloxycarbonyl-N³-[1-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)-hexyl-6-amino]-L-glutamate-α-amide 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:

(S)-2-tert-Butoxycarbonylamino-pentanedioic acid 5-benzyl ester 1-(2,5-dioxo-pyrrolidin-1-yl) ester (32886-40-1) + 6-aminohexyl 2,3,4-tri-O-benzyl-α-L-fucopyranoside p-toluenesulfonate → γ-benzyl N2-tert-butyloxycarbonyl-N3-[1-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)-hexyl-6-amino]-L-glutamate-α-amide (167016-50-4)

Guidance literature:

With 4-methyl-morpholine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1248/cpb.47.1237

Reference yield: 88.0%

γ-benzyl N2-tert-butyloxycarbonyl-N3-[1-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)-hexyl-6-amino]-L-glutamate-α-amide (167016-50-4) → N2-tert-butyloxycarbonyl-N3-[1-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)-hexyl-6-amino]-L-glutamate-α-amide (167016-51-5)

Guidance literature:

With cyclohexa-1,4-diene; palladium on activated charcoal; In ethanol; at 20 ℃; for 1h;

DOI:10.1248/cpb.47.1237

Reference yield:

γ-benzyl N2-tert-butyloxycarbonyl-N3-[1-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)-hexyl-6-amino]-L-glutamate-α-amide (167016-50-4) → [2-(6-{4-tert-butoxycarbonylamino-4-[6-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexylcarbamoyl]-butyrylamino}-hexyloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-acetic acid methyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / 1,4-cyclohexadiene / 10 percent Pd/C / ethanol / 1 h / 20 °C

2: HOSu; DCC; Et₃N / CH₂Cl₂ / 12 h / 0 °C

3: NaOMe / methanol / 2 h / 0 °C

With 1-hydroxy-pyrrolidine-2,5-dione; cyclohexa-1,4-diene; sodium methylate; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; 1: Hydrogenolysis / 2: Condensation / 3: Deacetylation;

DOI:10.1248/cpb.47.1237

upstream raw materials:

(S)-2-tert-Butoxycarbonylamino-pentanedioic acid 5-benzyl ester 1-(2,5-dioxo-pyrrolidin-1-yl) ester

Downstream raw materials:

N²-tert-butyloxycarbonyl-N³-[1-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)-hexyl-6-amino]-L-glutamate-α-amide

N²-tert-butyloxycarbonyl-N⁵-[6-2,4,6-tri-O-acetyl-3-O-methoxycarbonylmethyl-β-D-galactopyranosyl)hexyl]-N¹-[6-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)hexyl]-L-glutamin-α-amide