N^α-fluoren-9-ylmethoxycarbonyl-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester

Base Information

• Chemical Name: N^α-fluoren-9-ylmethoxycarbonyl-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester
• CAS No.: 215029-93-9
• Molecular Formula: C₃₉H₃₈N₄O₉
• Molecular Weight: 706.752

Synonyms:N^α-fluoren-9-ylmethoxycarbonyl-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester

Chemical Property of N^α-fluoren-9-ylmethoxycarbonyl-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester

Chemical Property:

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Technology Process of N^α-fluoren-9-ylmethoxycarbonyl-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester

There total 12 articles about N^α-fluoren-9-ylmethoxycarbonyl-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl 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: 95.0%

N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester (282736-09-8) → Nα-fluoren-9-ylmethoxycarbonyl-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester (215029-93-9)

Guidance literature:

With thiourea; In methanol;

DOI:10.1016/S0040-4039(00)00367-1

Reference yield: 73.0%

benzaldehyde dimethyl acetal (1125-88-8) + Nα-fluoren-9-ylmethoxycarbonyl-O-(2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester (218291-41-9) → Nα-fluoren-9-ylmethoxycarbonyl-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester (215029-93-9)

Guidance literature:

With toluene-4-sulfonic acid; In nitromethane; for 3h; Ambient temperature;

DOI:10.1021/ja9825128

Reference yield:

phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-D-galactopyranoside (150809-76-0) → Nα-fluoren-9-ylmethoxycarbonyl-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester (215029-93-9)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. NH₃ / methanol / 4 h / 20 °C

2: 19.4 g / p-TsOH / 3 h / 20 °C

3: 100 percent / NaHCO₃ / tetrahydrofuran / 20 °C

4: 76 percent / AgOTf; K₂CO₃; TMU / drierite / CH₂Cl₂ / 36 h / -10 - 25 °C

5: 95 percent / 2,6-lutidine; thiourea / methanol / 20 °C

With 2,6-dimethylpyridine; ammonium hydroxide; silver trifluoromethanesulfonate; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; thiourea; tetramethylurea; calcium sulfate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/1521-3765(20010202)7:3<585::AID-CHEM585>3.3.CO;2-Y

upstream raw materials:

benzaldehyde dimethyl acetal

N^α-fluoren-9-ylmethoxycarbonyl-O-(2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester

N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester

phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-D-galactopyranoside

Downstream raw materials:

N^α-fluoren-9-ylmethoxycarbonyl-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-threonine benzyl ester

C₄₇H₅₀N₄O₁₉

C₄₉H₅₄N₂O₂₀

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-threonine

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