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

Base Information

• Chemical Name: 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
• CAS No.: 167016-02-6
• Molecular Formula: C₆₄H₉₁N₃O₂₀
• Molecular Weight: 1222.43

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 3 articles about 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 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) → 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 (167016-02-6)

Guidance literature:

Multi-step reaction with 3 steps

1: N-methylmorpholine / CH₂Cl₂ / 1 h / 0 °C

2: 88 percent / 1,4-cyclohexadiene / 10 percent Pd/C / ethanol / 1 h / 20 °C

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

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

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) → 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 (167016-02-6)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1248/cpb.47.1237

Reference yield:

N2-tert-butyloxycarbonyl-N3-[1-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)-hexyl-6-amino]-L-glutamate-α-amide (167016-51-5) + 6-aminohexyl 2,4,6-tri-O-acetyl-3-O-methoxycarbonyl methyl-β-D-galactopyranoside, trifluoroacetic acid salt → 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 (167016-02-6)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1248/cpb.47.1237

upstream raw materials:

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

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

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

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