(2S,3S)-3-Benzyloxycarbonylamino-2-hydroxy-5-methyl-hexanoic acid

Base Information

• Chemical Name: (2S,3S)-3-Benzyloxycarbonylamino-2-hydroxy-5-methyl-hexanoic acid
• CAS No.: 82985-18-0
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.335
• Mol file: 82985-18-0.mol

Synonyms:(2S,3S)-3-Benzyloxycarbonylamino-2-hydroxy-5-methyl-hexanoic acid

Chemical Property of (2S,3S)-3-Benzyloxycarbonylamino-2-hydroxy-5-methyl-hexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-Benzyloxycarbonylamino-2-hydroxy-5-methyl-hexanoic acid

There total 5 articles about (2S,3S)-3-Benzyloxycarbonylamino-2-hydroxy-5-methyl-hexanoic 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: 100.0%

(2S,3S)-3-Benzyloxycarbonylamino-2-hydroxy-5-methyl-hexanoic acid methyl ester (126535-80-6) → (2S,3S)-3-Benzyloxycarbonylamino-2-hydroxy-5-methyl-hexanoic acid (82985-18-0)

Guidance literature:

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

DOI:10.1055/s-1989-27367

Reference yield:

phenylmethyl (4S)-4-(2-methylpropyl)-6-oxo-1,3-oxazinane-3-carboxylate (922705-34-8) → (2S,3S)-3-Benzyloxycarbonylamino-2-hydroxy-5-methyl-hexanoic acid (82985-18-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaHMDS / tetrahydrofuran; hexane / 0.67 h / -78 - -50 °C

1.2: 46 percent / MoO₅*pyridine*(Me₂N)3PO / tetrahydrofuran; hexane / -50 - -30 °C

2.1: 39 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 20 h / 20 °C

3.1: acetic acid; aq. HCl / 20 h / 45 °C

With hydrogenchloride; sodium hexamethyldisilazane; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; hexane; 2.1: Mitsunobu reaction;

DOI:10.1021/jo0700326

Reference yield:

(4S,5S)-N-benzyloxycarbonyl-5-hydroxy-4-isobutyl-1,3-oxazinan-6-one (937793-04-9) → (2S,3S)-3-Benzyloxycarbonylamino-2-hydroxy-5-methyl-hexanoic acid (82985-18-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 39 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 20 h / 20 °C

2: acetic acid; aq. HCl / 20 h / 45 °C

With hydrogenchloride; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1: Mitsunobu reaction;

DOI:10.1021/jo0700326

upstream raw materials:

(2S,3S)-3-Benzyloxycarbonylamino-2-hydroxy-5-methyl-hexanoic acid methyl ester

phenylmethyl (4S)-4-(2-methylpropyl)-6-oxo-1,3-oxazinane-3-carboxylate

(4S,5S)-N-benzyloxycarbonyl-5-hydroxy-4-isobutyl-1,3-oxazinan-6-one

N-Benzyloxycarbonyl-L-Homoleucine