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

Base Information

• Chemical Name: 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
• CAS No.: 282736-10-1
• Molecular Formula: C₅₃H₅₆N₄O₁₈
• Molecular Weight: 1037.04

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 11 articles about 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 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: 93.0%

1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose (13992-16-0,23661-28-1,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1,24404-53-3) + Nα-fluoren-9-ylmethoxycarbonyl-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester (215029-93-9) → Nα-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 (282736-10-1)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; acetonitrile; at -45 ℃;

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

Reference yield: 83.0%

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate (86520-63-0) + Nα-fluoren-9-ylmethoxycarbonyl-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester (215029-93-9) → Nα-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 (282736-10-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -40 ℃;

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

Reference yield: 66.8%

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,142831-80-9,127061-80-7) + Nα-fluoren-9-ylmethoxycarbonyl-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester (215029-93-9) → Nα-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 (282736-10-1)

Guidance literature:

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

DOI:10.1007/s10719-017-9781-8

upstream raw materials:

1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose

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

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

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

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-threonine

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