N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine

Base Information

• Chemical Name: N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine
• CAS No.: 174783-85-8
• Molecular Formula: C₄₇H₅₂N₂O₁₉
• Molecular Weight: 948.932

Synonyms:N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine

Chemical Property of N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine

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Technology Process of N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine

There total 5 articles about N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine 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: 79.0%

Nα-fluoren-9-ylmethoxycarbonyl-3-O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine phenacyl ester (848701-29-1) + acetic anhydride (108-24-7) → Nα-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine (174783-85-8)

Guidance literature:

With acetic acid; zinc; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1016/j.tetasy.2004.12.003

Reference yield:

(2S,4aR,7R,8R,8aR)-7-Azido-6-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol → Nα-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine (174783-85-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / TMSOTf / CH₂Cl₂ / -45 - 20 °C

2: 100 percent / triethylamine trihydrofluoride / tetrahydrofuran / 20 °C

3: 95 percent / DBU / CH₂Cl₂ / 0 °C

4: 80 percent / TMSOTf / CH₂Cl₂; tetrahydrofuran / 1 h / 20 °C

5: 79 percent / Zn; AcOH / tetrahydrofuran / 4 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; triethylamine trihydrofluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetasy.2004.12.003

Reference yield:

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate (86520-63-0) → Nα-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine (174783-85-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / TMSOTf / CH₂Cl₂ / -45 - 20 °C

2: 100 percent / triethylamine trihydrofluoride / tetrahydrofuran / 20 °C

3: 95 percent / DBU / CH₂Cl₂ / 0 °C

4: 80 percent / TMSOTf / CH₂Cl₂; tetrahydrofuran / 1 h / 20 °C

5: 79 percent / Zn; AcOH / tetrahydrofuran / 4 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; triethylamine trihydrofluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetasy.2004.12.003

upstream raw materials:

N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine phenacyl ester

acetic anhydride

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate

2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl 2,2,2-trichloroacetimidate

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