N^γ-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N^α-(fluoren-9-ylmethoxycarbonyl)-L-asparagine pentafluorophenyl ester

Base Information

• Chemical Name: N^γ-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N^α-(fluoren-9-ylmethoxycarbonyl)-L-asparagine pentafluorophenyl ester
• CAS No.: 132807-48-8
• Molecular Formula: C₃₉H₃₆F₅N₃O₁₃
• Molecular Weight: 849.719

Synonyms:N^γ-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N^α-(fluoren-9-ylmethoxycarbonyl)-L-asparagine pentafluorophenyl ester

Chemical Property of N^γ-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N^α-(fluoren-9-ylmethoxycarbonyl)-L-asparagine pentafluorophenyl ester

Chemical Property:

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Technology Process of N^γ-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N^α-(fluoren-9-ylmethoxycarbonyl)-L-asparagine pentafluorophenyl ester

There total 5 articles about N^γ-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N^α-(fluoren-9-ylmethoxycarbonyl)-L-asparagine pentafluorophenyl 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: 84.0%

2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine (4515-24-6) + Nα-(Fluoren-9-ylmethoxycarbonyl)-L-aspartic 4-Acid Chloride 1-pentafluorophenyl Ester (132785-38-7) → Nγ-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-Nα-(fluoren-9-ylmethoxycarbonyl)-L-asparagine pentafluorophenyl ester (132807-48-8)

Guidance literature:

With N-ethylmorpholine;; In tetrahydrofuran; at 0 ℃;

Reference yield: 81.0%

2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine (4515-24-6) + Nα-(Fluoren-9-ylmethoxycarbonyl)-L-aspartic 4-Acid Chloride 1-pentafluorophenyl Ester (132785-38-7) → Fmoc-Asn(Ac3GlcNAcβ1-N-)-O-Pfp (132807-48-8)

Guidance literature:

With N-ethylmorpholine;; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)97223-X

Reference yield:

tert-butyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-1-pentafluorophenyl L-aspartate (86061-01-0,200335-75-7) → Fmoc-Asn(Ac3GlcNAcβ1-N-)-O-Pfp (132807-48-8)

Guidance literature:

Multi-step reaction with 3 steps

1: TFA / 0.5 h

2: SOCl₂ / 1 h

3: 81 percent / N-ethylmorpholine / tetrahydrofuran

With N-ethylmorpholine;; thionyl chloride; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)97223-X

upstream raw materials:

2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine

N^α-(Fluoren-9-ylmethoxycarbonyl)-L-aspartic 4-Acid Chloride 1-pentafluorophenyl Ester

tert-butyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-1-pentafluorophenyl L-aspartate

N^α-Fmoc-L-Asn-OPfp

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