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: N²-tert-butyloxycarbonyl-N³-[1-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)-hexyl-6-amino]-L-glutamate-α-amide
• CAS No.: 167016-51-5
• Molecular Formula: C₄₃H₅₈N₂O₁₀
• Molecular Weight: 762.941

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

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

Chemical Property:

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

There total 2 articles about 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: 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:

(S)-2-tert-Butoxycarbonylamino-pentanedioic acid 5-benzyl ester 1-(2,5-dioxo-pyrrolidin-1-yl) ester (32886-40-1) → 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:

Multi-step reaction with 2 steps

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

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

With 4-methyl-morpholine; cyclohexa-1,4-diene; palladium on activated charcoal; In ethanol; dichloromethane; 1: Condensation / 2: Hydrogenolysis;

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 O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-benzoyl-β-D-galactopyranoside p-toluenesulfonate → N2-tert-butyloxycarbonyl-N5[6-[O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-benzoyl-β-D-galactopyranosyl]hexyl]...

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:

γ-benzyl 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

Downstream raw materials:

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

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

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