benzyl (2S)-6-(tert-butyloxycarbonylamino)-2-hydroxy-hexanoate

Base Information

• Chemical Name: benzyl (2S)-6-(tert-butyloxycarbonylamino)-2-hydroxy-hexanoate
• CAS No.: 368450-21-9
• Molecular Formula: C₁₈H₂₇NO₅
• Molecular Weight: 337.416
• Mol file: 368450-21-9.mol

Synonyms:benzyl (2S)-6-(tert-butyloxycarbonylamino)-2-hydroxy-hexanoate

Chemical Property of benzyl (2S)-6-(tert-butyloxycarbonylamino)-2-hydroxy-hexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S)-6-(tert-butyloxycarbonylamino)-2-hydroxy-hexanoate

There total 5 articles about benzyl (2S)-6-(tert-butyloxycarbonylamino)-2-hydroxy-hexanoate 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: 75.0%

benzyl bromide (100-39-0) + (S)-6-(tert-butyloxycarbonylamino)-2-hydroxyhexanoic acid (111223-31-5) → benzyl (2S)-6-(tert-butyloxycarbonylamino)-2-hydroxy-hexanoate (368450-21-9)

Guidance literature:

(S)-6-(tert-butyloxycarbonylamino)-2-hydroxyhexanoic acid; With caesium carbonate; In methanol; water; pH=7;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 6h; Further stages.;

DOI:10.1021/jo0006573

Reference yield:

N6-[(benzyloxy)carbonyl]-L-lysine (1155-64-2,57705-97-2,67178-46-5,25931-47-9) → benzyl (2S)-6-(tert-butyloxycarbonylamino)-2-hydroxy-hexanoate (368450-21-9)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/jo0006573

Reference yield:

(S)-6-[[(Phenylmethoxy)carbonyl]amino]-2-hydroxyhexanoic acid (59221-35-1) → benzyl (2S)-6-(tert-butyloxycarbonylamino)-2-hydroxy-hexanoate (368450-21-9)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jo0006573

upstream raw materials:

benzyl bromide

(S)-6-(tert-butyloxycarbonylamino)-2-hydroxyhexanoic acid

di-tert-butyl dicarbonate

N₆-[(benzyloxy)carbonyl]-L-lysine