N^α-fluoren-9-ylmethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloro-ethoxy-carbonylamino)-β-Dgalactopyranosyl]-L-threonine benzyl ester

Base Information

• Chemical Name: N^α-fluoren-9-ylmethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloro-ethoxy-carbonylamino)-β-Dgalactopyranosyl]-L-threonine benzyl ester
• CAS No.: 1380302-92-0
• Molecular Formula: C₄₁H₄₃Cl₃N₂O₁₄
• Molecular Weight: 894.156

Synonyms:N^α-fluoren-9-ylmethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloro-ethoxy-carbonylamino)-β-Dgalactopyranosyl]-L-threonine benzyl ester

Chemical Property of N^α-fluoren-9-ylmethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloro-ethoxy-carbonylamino)-β-Dgalactopyranosyl]-L-threonine benzyl ester

Chemical Property:

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Technology Process of N^α-fluoren-9-ylmethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloro-ethoxy-carbonylamino)-β-Dgalactopyranosyl]-L-threonine benzyl ester

There total 5 articles about N^α-fluoren-9-ylmethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloro-ethoxy-carbonylamino)-β-Dgalactopyranosyl]-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: 75.0%

N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester (73724-48-8) + 1-trichloroacetamido-2-deoxy-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-α-D-galactopyranose 3,4,6-triacetate (195142-26-8) → Nα-fluoren-9-ylmethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloro-ethoxy-carbonylamino)-β-Dgalactopyranosyl]-L-threonine benzyl ester (1380302-92-0)

Guidance literature:

N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester; 1-trichloroacetamido-2-deoxy-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-α-D-galactopyranose 3,4,6-triacetate; In dichloromethane; at 20 ℃; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; Inert atmosphere; Molecular sieve;

DOI:10.1007/s10719-011-9353-2

Reference yield:

2-deoxy-2[[(2,2,2-trichloroethoxy)carbonyl]amino]-D-galactopyranose 3,4,6-triacetate → Nα-fluoren-9-ylmethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloro-ethoxy-carbonylamino)-β-Dgalactopyranosyl]-L-threonine benzyl ester (1380302-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / Inert atmosphere

2.1: dichloromethane / 20 °C / Molecular sieve; Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere; Molecular sieve

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1007/s10719-011-9353-2

Reference yield:

2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-galactopyranose → Nα-fluoren-9-ylmethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloro-ethoxy-carbonylamino)-β-Dgalactopyranosyl]-L-threonine benzyl ester (1380302-92-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / Inert atmosphere

2.1: hydrazine; acetic acid / N,N-dimethyl-formamide / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / Inert atmosphere

4.1: dichloromethane / 20 °C / Molecular sieve; Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere; Molecular sieve

With pyridine; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; hydrazine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1007/s10719-011-9353-2

upstream raw materials:

D-(+)-galactosamine hydrochloride

1,3,4,6-Tetra-O-acetyl-2-(2,2,2-trichloroethoxycarbonylamino)-2-deoxy-α/β-D-galactopyranose

N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester

1-trichloroacetamido-2-deoxy-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-α-D-galactopyranose 3,4,6-triacetate

Downstream raw materials:

N^α-fluoren-9-ylmethoxycarbonyl-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranosyl)-L-threonine benzylester

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