benzyl (R)-6-(tert-butyloxycarbonylamino)-2-phthalimidooxyhexanoate

Base Information

• Chemical Name: benzyl (R)-6-(tert-butyloxycarbonylamino)-2-phthalimidooxyhexanoate
• CAS No.: 310404-51-4
• Molecular Formula: C₂₆H₃₀N₂O₇
• Molecular Weight: 482.533
• Mol file: 310404-51-4.mol

Synonyms:

Chemical Property of benzyl (R)-6-(tert-butyloxycarbonylamino)-2-phthalimidooxyhexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (R)-6-(tert-butyloxycarbonylamino)-2-phthalimidooxyhexanoate

There total 5 articles about benzyl (R)-6-(tert-butyloxycarbonylamino)-2-phthalimidooxyhexanoate 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:

N6-[(benzyloxy)carbonyl]-L-lysine (1155-64-2,57705-97-2,67178-46-5,25931-47-9) → benzyl (R)-6-(tert-butyloxycarbonylamino)-2-phthalimidooxyhexanoate (310404-51-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 95 percent / NaNO₂; 50percent HOAc / H₂O / 0.33 h / 0 °C

2.1: 88 percent / H₂ / Pd/C / methanol / 2 h / 760.05 Torr

3.1: 74 percent / 1N NaOH / dioxane / 2 h / 0 °C

4.1: Cs₂CO₃ / methanol; H₂O / pH 7

4.2: 75 percent / dimethylformamide / 6 h / 20 °C

5.1: 69 percent / PPh₃; DIAD / CH₂Cl₂ / 0.67 h / -40 - -20 °C

With sodium hydroxide; di-isopropyl azodicarboxylate; hydrogen; caesium carbonate; triphenylphosphine; sodium nitrite; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; water; 1.1: Substitution / 2.1: Hydrogenolysis / 3.1: Acylation / 4.1: deprotonation / 4.2: benzylation / 5.1: Substitution;

DOI:10.1021/jo0006573

Reference yield:

(S)-6-[[(Phenylmethoxy)carbonyl]amino]-2-hydroxyhexanoic acid (59221-35-1) → benzyl (R)-6-(tert-butyloxycarbonylamino)-2-phthalimidooxyhexanoate (310404-51-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 88 percent / H₂ / Pd/C / methanol / 2 h / 760.05 Torr

2.1: 74 percent / 1N NaOH / dioxane / 2 h / 0 °C

3.1: Cs₂CO₃ / methanol; H₂O / pH 7

3.2: 75 percent / dimethylformamide / 6 h / 20 °C

4.1: 69 percent / PPh₃; DIAD / CH₂Cl₂ / 0.67 h / -40 - -20 °C

With sodium hydroxide; di-isopropyl azodicarboxylate; hydrogen; caesium carbonate; triphenylphosphine; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; water; 1.1: Hydrogenolysis / 2.1: Acylation / 3.1: deprotonation / 3.2: benzylation / 4.1: Substitution;

DOI:10.1021/jo0006573

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → benzyl (R)-6-(tert-butyloxycarbonylamino)-2-phthalimidooxyhexanoate (310404-51-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 74 percent / 1N NaOH / dioxane / 2 h / 0 °C

2.1: Cs₂CO₃ / methanol; H₂O / pH 7

2.2: 75 percent / dimethylformamide / 6 h / 20 °C

3.1: 69 percent / PPh₃; DIAD / CH₂Cl₂ / 0.67 h / -40 - -20 °C

With sodium hydroxide; di-isopropyl azodicarboxylate; caesium carbonate; triphenylphosphine; In 1,4-dioxane; methanol; dichloromethane; water; 1.1: Acylation / 2.1: deprotonation / 2.2: benzylation / 3.1: Substitution;

DOI:10.1021/jo0006573

upstream raw materials:

di-tert-butyl dicarbonate

N₆-[(benzyloxy)carbonyl]-L-lysine

(S)-6-Amino-2-hydroxyhexanoic acid

(S)-6-[[(Phenylmethoxy)carbonyl]amino]-2-hydroxyhexanoic acid