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

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 allyl ester
• CAS No.: 905456-86-2
• Molecular Formula: C₇₆H₈₃N₃O₁₉
• Molecular Weight: 1342.5

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 allyl ester

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 allyl ester

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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 allyl ester

There total 7 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 allyl 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: 82.0%

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) + (S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid (144120-53-6) → 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)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

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 allyl ester (905456-86-2)

Guidance literature:

Multi-step reaction with 5 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

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; copper(ll) bromide; nickel; In dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1016/j.carres.2006.03.003

Reference yield:

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 (905456-82-8) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / hydrogen / Raney-nickel / propan-2-ol; H₂O / 5 h / pH 7

2: 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

With 1-hydroxy-7-aza-benzotriazole; hydrogen; N-ethyl-N,N-diisopropylamine; HATU; nickel; In water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1016/j.carres.2006.03.003

upstream raw materials:

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

(S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid

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

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

Downstream 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

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