N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-2-deoxy-4,6-O-benzylidene-3-O-[2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-β-D-galactopyranosyl])-α-D-galactopyranosyl-L-threonine-tert-butyl ester

Base Information

• Chemical Name: N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-2-deoxy-4,6-O-benzylidene-3-O-[2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-β-D-galactopyranosyl])-α-D-galactopyranosyl-L-threonine-tert-butyl ester
• CAS No.: 1191118-29-2
• Molecular Formula: C₅₀H₅₉FN₂O₁₇
• Molecular Weight: 979.02
• Mol file: 1191118-29-2.mol

Synonyms:N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-2-deoxy-4,6-O-benzylidene-3-O-[2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-β-D-galactopyranosyl])-α-D-galactopyranosyl-L-threonine-tert-butyl ester

Chemical Property of N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-2-deoxy-4,6-O-benzylidene-3-O-[2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-β-D-galactopyranosyl])-α-D-galactopyranosyl-L-threonine-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-2-deoxy-4,6-O-benzylidene-3-O-[2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-β-D-galactopyranosyl])-α-D-galactopyranosyl-L-threonine-tert-butyl ester

There total 4 articles about N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-2-deoxy-4,6-O-benzylidene-3-O-[2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-β-D-galactopyranosyl])-α-D-galactopyranosyl-L-threonine-tert-butyl 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: 98.0%

2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-α-D-galactopyranosyl bromide (35521-86-9) + N-fluorenylmethoxycarbonyl-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine tert-butyl ester (638207-70-2) → N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-2-deoxy-4,6-O-benzylidene-3-O-[2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-β-D-galactopyranosyl])-α-D-galactopyranosyl-L-threonine-tert-butyl ester (1191118-29-2)

Guidance literature:

N-fluorenylmethoxycarbonyl-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine tert-butyl ester; With mercury(II) cyanide; In nitromethane; dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-α-D-galactopyranosyl bromide; In nitromethane; dichloromethane; at 80 ℃; for 1h; Inert atmosphere; Microwave irradiation;

DOI:10.1002/chem.200903294

Reference yield:

1,2,3,4-tetra-O-acetyl-6-deoxy-6-fluoro-β-D-galactopyranose (118396-37-5,674782-58-2) → N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-2-deoxy-4,6-O-benzylidene-3-O-[2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-β-D-galactopyranosyl])-α-D-galactopyranosyl-L-threonine-tert-butyl ester (1191118-29-2)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen bromide; acetic acid / dichloromethane / 0 - 20 °C

2: mercury(II) cyanide / nitromethane; dichloromethane / 1 h / 80 °C / Molecular sieve; Microwave irradiation

With hydrogen bromide; mercury(II) cyanide; acetic acid; In nitromethane; dichloromethane;

DOI:10.1055/s-0029-1217566

Reference yield:

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-2-deoxy-4,6-O-benzylidene-3-O-[2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-β-D-galactopyranosyl])-α-D-galactopyranosyl-L-threonine-tert-butyl ester (1191118-29-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 2,6-dimethylpyridine; diethylamino-sulfur trifluoride / 1 h / 80 °C / Microwave irradiation

2: acetic acid / Reflux

3: hydrogen bromide; acetic acid / dichloromethane / 0 - 20 °C

4: mercury(II) cyanide / nitromethane; dichloromethane / 1 h / 80 °C / Molecular sieve; Microwave irradiation

With 2,6-dimethylpyridine; diethylamino-sulfur trifluoride; hydrogen bromide; mercury(II) cyanide; acetic acid; In nitromethane; dichloromethane;

DOI:10.1055/s-0029-1217566

upstream raw materials:

2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-α-D-galactopyranosyl bromide

N-fluorenylmethoxycarbonyl-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine tert-butyl ester

6-deoxy-6-fluoro-1,2:3,4-di-O-isopropylidene-α-D-galctopyranose

1,2,3,4-tetra-O-acetyl-6-deoxy-6-fluoro-β-D-galactopyranose