5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic acid

Base Information

• Chemical Name: 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic acid
• CAS No.: 98818-45-2
• Molecular Formula: C₂₄H₃₁NO₅
• Molecular Weight: 413.514
• Mol file: 98818-45-2.mol

Synonyms:5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic acid

Chemical Property of 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic acid

There total 28 articles about 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic 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: 95.0%

(3R,5S)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one (98818-41-8) → 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic acid (98818-45-2)

Guidance literature:

With sodium hydroxide; water; In 1,4-dioxane; Ambient temperature;

DOI:10.1135/cccc19980231

Reference yield:

α-bromo-p-toluidine (63516-03-0) → 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic acid (98818-45-2)

Guidance literature:

Multi-step reaction with 4 steps

1: NaOEt / ethanol / 18 h / Ambient temperature

2: aq. LiOH / ethanol / 5 h

3: toluene / 24 h / Heating

4: aq. LiOH / 1,2-dimethoxy-ethane / 3 h / Ambient temperature

With lithium hydroxide; sodium ethanolate; In 1,2-dimethoxyethane; ethanol; toluene;

DOI:10.1021/jm00088a004

Reference yield:

(S)-2-(N,N-dibenzylamino)-3-phenylpropanoic acid (95437-43-7) → 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic acid (98818-45-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 92 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide*HCl, hydroxybenztriazole hydrate, DMAP, Hunig's base / dimethylformamide / 2 h / Ambient temperature

2: 93 percent / tetrahydrofuran / 0 °C

3: NaBH₄ / methanol / 0 °C

4: 92 percent / 3N HCl / tetrahydrofuran

5: 95 percent / CrO₃*H₂SO₄ / acetone / 0 °C

6: 78 percent / 0 °C

7: HCO₂H / Pd (black) / methanol

8: NEt₃ / dimethylformamide

9: 1.) 1N NaOH, 2.) citric acid / tetrahydrofuran

With chromium(VI) oxide; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; formic acid; sulfuric acid; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; citric acid; palladium; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)73701-4

upstream raw materials:

(3R,5S)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one

Boc-L-phenylalaninal

(3S,5S)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one

(1,4-dibenzyl-2-oxo-pent-4-enyl)-carbamic acid tert-butyl ester

Downstream raw materials:

{(1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(1S,2S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester

{(1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-3-carbamoyl-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-propylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester

(S)-4-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoylamino]-4-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-butyric acid benzyl ester

(2R,4S,5S)-N,2-dibenzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanamide