(5R)-N^α-(fluoren-9-ylmethoxycarbonyl)-N^ε-benzyloxycarbonyl-5-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-5-hydroxy-L-lysine

Base Information

• Chemical Name: (5R)-N^α-(fluoren-9-ylmethoxycarbonyl)-N^ε-benzyloxycarbonyl-5-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-5-hydroxy-L-lysine
• CAS No.: 270089-67-3
• Molecular Formula: C₄₃H₄₈N₂O₁₆
• Molecular Weight: 848.858

Synonyms:(5R)-N^α-(fluoren-9-ylmethoxycarbonyl)-N^ε-benzyloxycarbonyl-5-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-5-hydroxy-L-lysine

Chemical Property of (5R)-N^α-(fluoren-9-ylmethoxycarbonyl)-N^ε-benzyloxycarbonyl-5-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-5-hydroxy-L-lysine

Chemical Property:

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Technology Process of (5R)-N^α-(fluoren-9-ylmethoxycarbonyl)-N^ε-benzyloxycarbonyl-5-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-5-hydroxy-L-lysine

There total 11 articles about (5R)-N^α-(fluoren-9-ylmethoxycarbonyl)-N^ε-benzyloxycarbonyl-5-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-5-hydroxy-L-lysine 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: 48.0%

(5R)-Nα-(fluoren-9-ylmethoxycarbonyl)-Nε-benzyloxycarbonyl-5-hydroxy-L-lysine diphenyl-methyl ester + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → (5R)-Nα-(fluoren-9-ylmethoxycarbonyl)-Nε-benzyloxycarbonyl-5-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-5-hydroxy-L-lysine (270089-67-3)

Guidance literature:

(5R)-N^α-(fluoren-9-ylmethoxycarbonyl)-N^ε-benzyloxycarbonyl-5-hydroxy-L-lysine diphenyl-methyl ester; 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside; With molecular sieve; silver silicate; In dichloromethane; at -10 ℃; for 17h;

With water; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.666667h;

DOI:10.1016/S0040-4020(00)00061-2

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (2S,5R)-2-Amino-6-benzyloxycarbonylamino-5-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid (851857-30-2) → (5R)-Nα-(fluoren-9-ylmethoxycarbonyl)-Nε-benzyloxycarbonyl-5-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-5-hydroxy-L-lysine (270089-67-3)

Guidance literature:

With sodium hydrogencarbonate; In acetone; at 20 ℃; for 5h;

DOI:10.1016/j.tet.2004.04.081

Reference yield:

Caesium; (2S,5R)-6-benzyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-hexanoate → (5R)-Nα-(fluoren-9-ylmethoxycarbonyl)-Nε-benzyloxycarbonyl-5-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-5-hydroxy-L-lysine (270089-67-3)

Guidance literature:

Multi-step reaction with 3 steps

1: dimethylformamide / 20 °C

2: 82 percent / silver silicate; molecular sieves / CH₂Cl₂ / 0 °C

3: 86 percent / N-methylaniline / (PPh₃)4Pd⁽⁰⁾ / tetrahydrofuran / 1.5 h / 20 °C

With molecular sieve; silver silicate; N-methylaniline; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: glycosylation / 3: deallylation;

DOI:10.1016/S0040-4020(00)00061-2

upstream raw materials:

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(2S,5R)-2-Amino-6-benzyloxycarbonylamino-5-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid

1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose

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