6-(N-Benzyloxy-acetimidoyloxy)-2-benzyloxycarbonylamino-hexanoic acid benzyl ester

Base Information

• Chemical Name: 6-(N-Benzyloxy-acetimidoyloxy)-2-benzyloxycarbonylamino-hexanoic acid benzyl ester
• CAS No.: 81505-54-6
• Molecular Formula: C₃₀H₃₄N₂O₆
• Molecular Weight: 518.61
• Mol file: 81505-54-6.mol

Synonyms:6-(N-Benzyloxy-acetimidoyloxy)-2-benzyloxycarbonylamino-hexanoic acid benzyl ester

Chemical Property of 6-(N-Benzyloxy-acetimidoyloxy)-2-benzyloxycarbonylamino-hexanoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(N-Benzyloxy-acetimidoyloxy)-2-benzyloxycarbonylamino-hexanoic acid benzyl ester

There total 6 articles about 6-(N-Benzyloxy-acetimidoyloxy)-2-benzyloxycarbonylamino-hexanoic acid 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: 65.0%

N-benzyloxyacetamide (4797-81-3) + (D,L)-N-Cbz-ε-bromonorleucine benzyl ester (81505-58-0) → (D,L)-N2-Cbz-N6-(benzyloxy)lysine benzyl ester (81505-50-2) + 6-(N-Benzyloxy-acetimidoyloxy)-2-benzyloxycarbonylamino-hexanoic acid benzyl ester (81505-54-6)

Guidance literature:

With potassium carbonate; potassium iodide; In acetone; for 24h; Heating;

DOI:10.1021/ja00375a025

Reference yield:

rac-6-hydroxynorleucine (5462-80-6) → 6-(N-Benzyloxy-acetimidoyloxy)-2-benzyloxycarbonylamino-hexanoic acid benzyl ester (81505-54-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 84.3 percent / NaHCO₃, NaOH, pH 8.6 / 2.5 h

2: 86 percent / 18 h / Ambient temperature

3: 89 percent / CBr₄, PPh₃ / tetrahydrofuran / 12 h / Ambient temperature

4: 13 percent / KI, K₂CO₃ / acetone / 24 h / Heating

With sodium hydroxide; carbon tetrabromide; sodium hydrogencarbonate; potassium carbonate; triphenylphosphine; potassium iodide; In tetrahydrofuran; acetone;

DOI:10.1021/ja00375a025

Reference yield:

(D,L)-Cbz-ε-hydroxynorleucine (32245-65-1) → 6-(N-Benzyloxy-acetimidoyloxy)-2-benzyloxycarbonylamino-hexanoic acid benzyl ester (81505-54-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / 18 h / Ambient temperature

2: 89 percent / CBr₄, PPh₃ / tetrahydrofuran / 12 h / Ambient temperature

3: 13 percent / KI, K₂CO₃ / acetone / 24 h / Heating

With carbon tetrabromide; potassium carbonate; triphenylphosphine; potassium iodide; In tetrahydrofuran; acetone;

DOI:10.1021/ja00375a025

upstream raw materials:

N-benzyloxyacetamide

(D,L)-N-Cbz-ε-bromonorleucine benzyl ester

(D,L)-N-Cbz-ε-hydroxynorleucine benzyl ester

rac-6-hydroxynorleucine