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

Base Information

• Chemical Name: (S)-6-(tert-butyloxycarbonylamino)-2-hydroxyhexanoic acid
• CAS No.: 111223-31-5
• Molecular Formula: C₁₁H₂₁NO₅
• Molecular Weight: 247.291
• Mol file: 111223-31-5.mol

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

Chemical Property of (S)-6-(tert-butyloxycarbonylamino)-2-hydroxyhexanoic acid

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-6-(tert-butyloxycarbonylamino)-2-hydroxyhexanoic acid

There total 5 articles about (S)-6-(tert-butyloxycarbonylamino)-2-hydroxyhexanoic acid 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: 85.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-6-Amino-2-hydroxyhexanoic acid (42491-84-9) → (S)-6-(tert-butyloxycarbonylamino)-2-hydroxyhexanoic acid (111223-31-5)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 0 ℃; for 2h;

DOI:10.1055/s-0029-1216837

Reference yield: 73.0%

(S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid (2418-95-3) → (S)-6-(tert-butyloxycarbonylamino)-2-hydroxyhexanoic acid (111223-31-5)

Guidance literature:

With acetic acid; sodium nitrite; In water; at 0 - 20 ℃; for 4.5h;

DOI:10.1021/jacs.5b04681

Reference yield:

N6-[(benzyloxy)carbonyl]-L-lysine (1155-64-2,57705-97-2,67178-46-5,25931-47-9) → (S)-6-(tert-butyloxycarbonylamino)-2-hydroxyhexanoic acid (111223-31-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / NaNO₂; 50percent HOAc / H₂O / 0.33 h / 0 °C

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

3: 74 percent / 1N NaOH / dioxane / 2 h / 0 °C

With sodium hydroxide; hydrogen; sodium nitrite; palladium on activated charcoal; In 1,4-dioxane; methanol; water; 1: Substitution / 2: Hydrogenolysis / 3: Acylation;

DOI:10.1021/jo0006573

upstream raw materials:

di-tert-butyl dicarbonate

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

N₆-[(benzyloxy)carbonyl]-L-lysine

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

Downstream raw materials:

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

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

L-O-lysine(Boc)-D-alanine benzyl ester

L-O-lysine(Boc)-L-valine benzyl ester