N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-3-O-[2,3,4,6-tetra-O-(3-fluorobenzoyl)-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester

Base Information

• Chemical Name: N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-3-O-[2,3,4,6-tetra-O-(3-fluorobenzoyl)-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester
• CAS No.: 343309-01-3
• Molecular Formula: C₅₉H₄₀F₉NO₁₄
• Molecular Weight: 1157.95

Synonyms:N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-3-O-[2,3,4,6-tetra-O-(3-fluorobenzoyl)-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester

Chemical Property of N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-3-O-[2,3,4,6-tetra-O-(3-fluorobenzoyl)-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester

Chemical Property:

Purity/Quality:

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Technology Process of N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-3-O-[2,3,4,6-tetra-O-(3-fluorobenzoyl)-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester

There total 2 articles about N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-3-O-[2,3,4,6-tetra-O-(3-fluorobenzoyl)-β-D-glucopyranosyl]-L-serine pentafluorophenyl 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: 87.0%

Nα-(fluoren-9-ylmethoxycarbonyl)-Nα-methyl-L-serine pentafluorophenyl ester (291311-49-4) + 2,3,4,6-tetra-O-(3-fluorobenzoyl)-α-D-glucopyranosyl bromide (343308-93-0) → Nα-(fluoren-9-ylmethoxycarbonyl)-Nα-methyl-3-O-[2,3,4,6-tetra-O-(3-fluorobenzoyl)-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester (343309-01-3)

Guidance literature:

With 3 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 2.5h;

DOI:10.1021/jo001584q

Reference yield:

1,2,3,4,6-penta-O-(3-fluorobenzoyl)-D-glucopyranose (153215-07-7) → Nα-(fluoren-9-ylmethoxycarbonyl)-Nα-methyl-3-O-[2,3,4,6-tetra-O-(3-fluorobenzoyl)-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester (343309-01-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / HBr / acetic acid; acetic anhydride / 4.5 h / 50 °C

2: 87 percent / AgOTf; powdered molecular sieves 3 Angstrem / CH₂Cl₂ / 2.5 h / 0 °C

With 3 A molecular sieve; hydrogen bromide; silver trifluoromethanesulfonate; In dichloromethane; acetic anhydride; acetic acid;

DOI:10.1021/jo001584q

Reference yield: 68.0%

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3,136132-75-7) + N-Fmoc L-Phe (35661-40-6) + Nα-(fluoren-9-ylmethoxycarbonyl)-Nα-methyl-3-O-[2,3,4,6-tetra-O-(3-fluorobenzoyl)-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester (343309-01-3) → Nα-acetyl-L-alanyl-Nα-methyl-3-O-[2,3,4,6-tetra-O-(3-fluorobenzoyl)-β-D-glucopyranosyl]-L-seryl-L-phenylalanine amide (343309-05-7)

Guidance literature:

Multistep reaction.;

DOI:10.1021/jo001584q

upstream raw materials:

N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-L-serine pentafluorophenyl ester

2,3,4,6-tetra-O-(3-fluorobenzoyl)-α-D-glucopyranosyl bromide

1,2,3,4,6-penta-O-(3-fluorobenzoyl)-D-glucopyranose

Downstream raw materials:

N^α-acetyl-L-alanyl-N^α-methyl-3-O-[2,3,4,6-tetra-O-(3-fluorobenzoyl)-β-D-glucopyranosyl]-L-seryl-L-phenylalanine amide

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