N^α-fluorenylmethoxycarbonyl-N^ω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine

Base Information

• Chemical Name: N^α-fluorenylmethoxycarbonyl-N^ω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine
• CAS No.: 905456-87-3
• Molecular Formula: C₇₃H₇₉N₃O₁₉
• Molecular Weight: 1302.44

Synonyms:N^α-fluorenylmethoxycarbonyl-N^ω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine

Chemical Property of N^α-fluorenylmethoxycarbonyl-N^ω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine

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Technology Process of N^α-fluorenylmethoxycarbonyl-N^ω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine

There total 8 articles about N^α-fluorenylmethoxycarbonyl-N^ω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine 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: 74.0%

Nα-fluorenylmethoxycarbonyl-Nω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine allyl ester (905456-86-2) → Nα-fluorenylmethoxycarbonyl-Nω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine (905456-87-3)

Guidance literature:

With N-methylaniline; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.carres.2006.03.003

Reference yield:

2-acetamido-3-O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide (290330-37-9) → Nα-fluorenylmethoxycarbonyl-Nω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine (905456-87-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / 4 Angstroem molecular sieves; trifluoromethanesulfonic acid; triethylsilane / CH₂Cl₂ / 3 h / -78 °C

2: 84 percent / 3 Angstroem molecular sieves; tetrabutylammonium bromide; CuBr₂ / CH₂Cl₂ / 144 h / 20 °C

3: 88 percent / Na; methanol / 20 h / 20 °C

4: 100 percent / hydrogen / Raney-nickel / propan-2-ol; H₂O / 5 h / pH 7

5: 82 percent / O-(7-aza-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium PF₆; 1-hydroxy-7-aza-benzotriazole; diisopropylethylamine / dimethylformamide / 18 h / 20 °C

6: 74 percent / N-methylaniline / Pd(PPh₃)4 / tetrahydrofuran / 20 °C

With methanol; triethylsilane; 1-hydroxy-7-aza-benzotriazole; trifluorormethanesulfonic acid; 3 A molecular sieve; 4 A molecular sieve; tetrabutylammomium bromide; hydrogen; sodium; N-ethyl-N,N-diisopropylamine; HATU; N-methylaniline; copper(ll) bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; nickel; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1016/j.carres.2006.03.003

Reference yield:

N-[(2R,3R,4R,5S,6R)-2-Amino-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-6-benzyloxymethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-5-((2S,3S,4R,5R)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide (905456-85-1) → Nα-fluorenylmethoxycarbonyl-Nω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine (905456-87-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / O-(7-aza-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium PF₆; 1-hydroxy-7-aza-benzotriazole; diisopropylethylamine / dimethylformamide / 18 h / 20 °C

2: 74 percent / N-methylaniline / Pd(PPh₃)4 / tetrahydrofuran / 20 °C

With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU; N-methylaniline; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2006.03.003

upstream raw materials:

N^α-fluorenylmethoxycarbonyl-N^ω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine allyl ester

2-acetamido-3-O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide

N-[(2R,3R,4R,5S,6R)-2-Amino-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-6-benzyloxymethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-5-((2S,3S,4R,5R)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl azide

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