(2R,3r)-2-amino-3-hydroxy-4-methyl-valeric acid

Base Information

• Chemical Name: (2R,3r)-2-amino-3-hydroxy-4-methyl-valeric acid
• CAS No.: 87421-24-7
• Molecular Formula: C6H13NO3
• Molecular Weight: 147.174
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID70449109
• Nikkaji Number: J282.068D
• Mol file: 87421-24-7.mol

Synonyms:87421-24-7;(2R,3r)-2-amino-3-hydroxy-4-methyl-valeric acid;(2r,3r)-2-amino-3-hydroxy-4-methylpentanoic acid;D-Leucine, 3-hydroxy-, (3R)-;(3R)-3-Hydroxy-D-leucine;SCHEMBL1253160;DTXSID70449109;(2R,3R)-3-HYDROXYLEUCINE;AKOS017343067;(2R,3R)-2-Amino-3-hydroxy-4-methylpentanoic acid (non-preferred name)

Chemical Property of (2R,3r)-2-amino-3-hydroxy-4-methyl-valeric acid

Chemical Property:

• PSA: 83.55000
• LogP: 0.11550
• XLogP3: -2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 147.08954328
• Heavy Atom Count: 10
• Complexity: 124

Purity/Quality:

99% ^*data from raw suppliers

(2R,3R)-2-AMINO-3-HYDROXY-4-METHYL-PENTANOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(C(=O)O)N)O
• Isomeric SMILES: CC(C)[C@H]([C@H](C(=O)O)N)O
• Uses: (3R)-3-Hydroxy-D-leucine is a component of cyclodepsipeptides, papuamides and polyoxypeptins. It is also used in the synthesis of lactacystin.

Technology Process of (2R,3r)-2-amino-3-hydroxy-4-methyl-valeric acid

There total 82 articles about (2R,3r)-2-amino-3-hydroxy-4-methyl-valeric 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: 93.0%

C31H33N3NiO4 → (2S,3R)-3-hydroxyleucine (5817-22-1,6645-45-0,10148-70-6,28908-11-4,35016-54-7,35016-62-7,87421-23-6,87421-24-7,10148-71-7)

Guidance literature:

With hydrogenchloride; In methanol; for 1h; Inert atmosphere; Reflux;

DOI:10.1021/ol503507g

Reference yield: 80.0%

isobutyraldehyde (78-84-2) → (2S,3R)-3-hydroxyleucine (5817-22-1,6645-45-0,10148-70-6,28908-11-4,35016-54-7,35016-62-7,87421-23-6,87421-24-7,10148-71-7) + (S)-2-N-(N-benzyl-L-prolyl)aminobenzophenone hydrochloride

Guidance literature:

isobutyraldehyde; Ni(II)-(S)-o-[N-(N'-benzylprolyl)amino]benzophenone/glycine Schiff base complex; With sodium hydride; In tetrahydrofuran; at 16 ℃; for 0.166667h;

With hydrogenchloride; In methanol; Heating;

DOI:10.1016/S0957-4166(01)00071-4

Reference yield: 42.0%

L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + isobutyraldehyde (78-84-2) → (2S,3R)-3-hydroxyleucine (5817-22-1,6645-45-0,10148-70-6,28908-11-4,35016-54-7,35016-62-7,87421-23-6,87421-24-7,10148-71-7) + (2S,3S)-3-hydroxyleucine (10148-70-6)

Guidance literature:

With L-threonine transaldolase; In methanol; at 37 ℃; for 18h; pH=8.5; diastereoselective reaction; Enzymatic reaction;

DOI:10.1002/cbic.202100577

upstream raw materials:

(+/-)-erythro-2-bromo-3-hydroxy-4-methyl-valeric acid

N-Benzyl-DL-erythro-β-hydroxy-leucin

isobutyraldehyde

glycine

Downstream raw materials:

(+/-)-erythro-2-benzamino-3-hydroxy-4-methyl-valeric acid

5-Isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

rac-threo-3-Hydroxyleucin-N-sulfamat Natriumsalz

(2S,3S)-3-hydroxyleucine