BOC-(2S,3R)-3-AMINO-2-HYDROXY-5-METHYLHEXANOIC ACID

Base Information

• Chemical Name: BOC-(2S,3R)-3-AMINO-2-HYDROXY-5-METHYLHEXANOIC ACID
• CAS No.: 73397-25-8
• Molecular Formula: C₁₂H₂₃NO₅
• Molecular Weight: 261.318
• Hs Code.: 2924199090
• Mol file: 73397-25-8.mol

Synonyms:Hexanoicacid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-5-methyl-, [S-(R*,S*)]-

Chemical Property of BOC-(2S,3R)-3-AMINO-2-HYDROXY-5-METHYLHEXANOIC ACID

Chemical Property:

• PSA: 95.86000
• LogP: 1.76220
• Storage Temp.: -20°C

Purity/Quality:

98%min ^*data from raw suppliers

N-Boc-(2S,3R)-2-hydroxy-3-amino-5-methylhexanoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Boc-(2S,3R)-2-Hydroxy-3-Amino-5-Methylhexanoic Acid is a useful reagent/building block in the preparation of bestatin(PfA-?M1 inhibitor) and it’s derivatives from natural and unnatural N-?Boc-?D-?amino acids.

Technology Process of BOC-(2S,3R)-3-AMINO-2-HYDROXY-5-METHYLHEXANOIC ACID

There total 14 articles about BOC-(2S,3R)-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: 100.0%

(2S,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid Methyl Ester (73397-29-2) → (2S,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid (73397-25-8)

Guidance literature:

With sodium hydroxide; water; In 1,4-dioxane; pH 10;

DOI:10.1021/jo01300a004

Reference yield: 73.0%

N-(tert-butyloxycarbonyl) azide (1070-19-5) + (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) → (2RS,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid (73397-25-8,73397-26-9,73397-27-0,73397-28-1,77119-88-1)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; at 25 ℃;

DOI:10.1021/jo01300a004

Reference yield:

N-(tert-butyloxycarbonyl) azide (1070-19-5) → (2S,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid (73397-25-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / triethylamine / H₂O; dioxane / 25 °C

2: 60 percent / diethyl ether / 1 h / 25 °C

3: 100 percent / sodium hydroxide, water / dioxane / pH 10

With sodium hydroxide; water; triethylamine; In 1,4-dioxane; diethyl ether; water;

DOI:10.1021/jo01300a004

upstream raw materials:

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

N-(tert-butyloxycarbonyl) azide

(R)-4-methyl-1-oxopentane-2-benzylcarbamate

[(S)-1-((S)-Cyano-hydroxy-methyl)-3-methyl-butyl]-carbamic acid benzyl ester

Downstream raw materials:

(2R,3S)-3-amino-2-hydroxy-5-methylhexanoic acid

(2S,3S)-3-Amino-2-hydroxy-5-methylhexanoic Acid

(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-5-methylhexanoic acid

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