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

Base Information

• Chemical Name: 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
• CAS No.: 848701-29-1
• Molecular Formula: C₅₃H₅₄N₄O₁₉
• Molecular Weight: 1051.03

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 4 articles about 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 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: 80.0%

N-Fmoc serine phenacyl ester (125760-26-1) + 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 (618115-57-4) → 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)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; at 20 ℃; for 1h;

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-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)

Guidance literature:

Multi-step reaction with 4 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

With trimethylsilyl trifluoromethanesulfonate; triethylamine trihydrofluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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-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)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1016/j.tetasy.2004.12.003

upstream raw materials:

N-Fmoc serine phenacyl ester

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

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

Downstream raw materials:

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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