Nα-(4-nitrophenyloxycarbonyl)-Nε-(9-fluorenylmethoxycarbonyl)-D-Lys allyl ester

Base Information

• Chemical Name: Nα-(4-nitrophenyloxycarbonyl)-Nε-(9-fluorenylmethoxycarbonyl)-D-Lys allyl ester
• CAS No.: 850863-77-3
• Molecular Formula: C₃₁H₃₁N₃O₈
• Molecular Weight: 573.602
• Mol file: 850863-77-3.mol

Synonyms:Nα-(4-nitrophenyloxycarbonyl)-Nε-(9-fluorenylmethoxycarbonyl)-D-Lys allyl ester

Chemical Property of Nα-(4-nitrophenyloxycarbonyl)-Nε-(9-fluorenylmethoxycarbonyl)-D-Lys allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Nα-(4-nitrophenyloxycarbonyl)-Nε-(9-fluorenylmethoxycarbonyl)-D-Lys allyl ester

There total 3 articles about Nα-(4-nitrophenyloxycarbonyl)-Nε-(9-fluorenylmethoxycarbonyl)-D-Lys allyl 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: 91.0%

4-Nitrophenyl chloroformate (7693-46-1) + Boc-D-Lys(Fmoc)-OH allyl ester (850863-84-2) → Nα-(4-nitrophenyloxycarbonyl)-Nε-(9-fluorenylmethoxycarbonyl)-D-Lys allyl ester (850863-77-3)

Guidance literature:

Boc-D-Lys(Fmoc)-OH allyl ester; With toluene-4-sulfonic acid; In ethanol; dichloromethane; at 40 ℃; for 3h;

4-Nitrophenyl chloroformate; With pyridine; In dichloromethane; at 4 ℃; for 3h; Cooling with ice;

DOI:10.1021/acs.jnatprod.1c00336

Reference yield:

(R)-2-amino-6-(((benzyloxy)carbonyl)amino)hexanoic acid (34404-32-5,1155-64-2,32302-83-3,57705-97-2,67178-46-5,25931-47-9) → Nα-(4-nitrophenyloxycarbonyl)-Nε-(9-fluorenylmethoxycarbonyl)-D-Lys allyl ester (850863-77-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / NaOH / dioxane; H₂O / 1.5 h / 4 °C

2: 1.) H₂, 2.) aq. NaHCO₃ / 1.) Pd on carbon / 1) ethanol, overnight; 2) dioxane, ice-bath, 70 min

3: 1.) cesium carbonate / 1) DMF, 1 h; 2) DMF, 1 h

4: 1.) p-toluenesulfonic acid, 2.) pyridine / 1) dichloromethane, ethanol, 45 deg C (evaporating under reduced pressure); 2) CH₂Cl₂, ice/salt bath --> 5 deg C, 3 h

With pyridine; sodium hydroxide; hydrogen; sodium hydrogencarbonate; caesium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In 1,4-dioxane; water;

DOI:10.1021/jo970671o

Reference yield:

(2R)-2-(tert-butoxycarbonylamino)-6-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid (115186-31-7) → Nα-(4-nitrophenyloxycarbonyl)-Nε-(9-fluorenylmethoxycarbonyl)-D-Lys allyl ester (850863-77-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) cesium carbonate / 1) DMF, 1 h; 2) DMF, 1 h

2: 1.) p-toluenesulfonic acid, 2.) pyridine / 1) dichloromethane, ethanol, 45 deg C (evaporating under reduced pressure); 2) CH₂Cl₂, ice/salt bath --> 5 deg C, 3 h

With pyridine; caesium carbonate; toluene-4-sulfonic acid;

DOI:10.1021/jo970671o

upstream raw materials:

4-Nitrophenyl chloroformate

Boc-D-Lys(Fmoc)-OH allyl ester

(R)-2-amino-6-(((benzyloxy)carbonyl)amino)hexanoic acid

(2R)-2-(tert-butoxycarbonylamino)-6-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid

Downstream raw materials:

C₆₂H₈₂N₁₀O₁₂