3-amino-2-hydroxy-5-methylhexanoic acid

Base Information

• Chemical Name: 3-amino-2-hydroxy-5-methylhexanoic acid
• CAS No.: 62023-30-7
• Molecular Formula: C₇H₁₅NO₃
• Molecular Weight: 161.201
• Hs Code.: 2922509090
• Mol file: 62023-30-7.mol

Synonyms:Hexanoic acid,3-amino-2-hydroxy-5-methyl;Norstatine;

Chemical Property of 3-amino-2-hydroxy-5-methylhexanoic acid

Chemical Property:

• Vapor Pressure: 7.84E-06mmHg at 25°C
• Boiling Point: 336.3°Cat760mmHg
• PKA: 3.04±0.34(Predicted)
• Flash Point: 157.2°C
• PSA: 83.55000
• Density: 1.143g/cm³
• LogP: 0.50560

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-amino-2-hydroxy-5-methylhexanoic acid

There total 11 articles about 3-amino-2-hydroxy-5-methylhexanoic 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: 90.0%

[(S)-1-((S)-Cyano-hydroxy-methyl)-3-methyl-butyl]-carbamic acid benzyl ester (63219-62-5,73397-23-6,73397-24-7,106868-70-6,106868-79-5) → (2RS,3R)-3-Amino-2-hydroxy-5-methylhexanoic Acid (62023-30-7,70853-11-1,70853-17-7,73397-20-3,73397-21-4,75556-30-8)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 12h; Heating;

DOI:10.1021/jo01300a004

Reference yield:

(R)-4-methyl-1-oxopentane-2-benzylcarbamate (70853-26-8) → (2RS,3R)-3-Amino-2-hydroxy-5-methylhexanoic Acid (62023-30-7,70853-11-1,70853-17-7,73397-20-3,73397-21-4,75556-30-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaHSO₃ / 1.) 5 deg C, overnight, 2.) ethyl acetate, water, room temp., 4 h

2: 90 percent / concentrated HCl / dioxane / 12 h / Heating

With hydrogenchloride; sodium hydrogensulfite; In 1,4-dioxane;

DOI:10.1021/jo01300a004

Reference yield:

Cbz-D-Leu-OMe (73397-22-5) → (2RS,3R)-3-Amino-2-hydroxy-5-methylhexanoic Acid (62023-30-7,70853-11-1,70853-17-7,73397-20-3,73397-21-4,75556-30-8)

Guidance literature:

Multi-step reaction with 3 steps

1: Diisobutylaluminum hydride / toluene / 0.1 h / -78 °C

2: 1.) NaHSO₃ / 1.) 5 deg C, overnight, 2.) ethyl acetate, water, room temp., 4 h

3: 90 percent / concentrated HCl / dioxane / 12 h / Heating

With hydrogenchloride; diisobutylaluminium hydride; sodium hydrogensulfite; In 1,4-dioxane; toluene;

DOI:10.1021/jo01300a004

upstream raw materials:

N-tert-butoxycarbonyl-L-leucine methyl ester

potassium cyanide

methyl DL-threo-3-amino-2-hydroxy-5-methylhexanoate

(E)-methyl 5-methyl-2-hexenoate

Downstream raw materials:

amastatin

(2R,3R)-(3-Amino-2-hydroxy-5-methylhexanoyl)-L-valyl-L-valyl-L-aspartic Acid

(2R,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid

(2S,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid

Refernces

• 1、 Rich, Daniel H.,Moon, Byung Jo,Boparai, Amrit S.. "Synthesis of (2S,3R)-3-Amino-2-hydroxy-5-methylhexanoic Acid Derivatives. Application to the Synthesis of Amastatin, an Inhibitor of Aminopeptidases". . p. 2288 - 2290. Retrieved 2007/10/02.