(2r,3s)-2-amino-3-hydroxyhexanoic Acid

Base Information

• Chemical Name: (2r,3s)-2-amino-3-hydroxyhexanoic Acid
• CAS No.: 59286-25-8
• Molecular Formula: C₆H₁₃NO₃
• Molecular Weight: 147.174
• DSSTox Substance ID: DTXSID80546658
• Wikidata: Q82424556
• Mol file: 59286-25-8.mol

Synonyms:(2r,3s)-2-amino-3-hydroxyhexanoic Acid;59286-25-8;(2R,3S)-3-HYDROXYNORLEUCINE;(3S)-3-Hydroxy-D-norleucine;(2R,3S)-2-Amino-3-hydroxy-hexanoic acid;DTXSID80546658;(2r,3s)-2-amino-3-hydroxyhexanoicAcid

Chemical Property of (2r,3s)-2-amino-3-hydroxyhexanoic Acid

Chemical Property:

• Melting Point: >153oC (dec.)
• Storage Temp.: Refrigerator
• Solubility.: Water (Slightly)
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 147.08954328
• Heavy Atom Count: 10
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

(2R,3S)-3-Hydroxynorleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCC(C(C(=O)O)N)O
• Isomeric SMILES: CCC[C@@H]([C@H](C(=O)O)N)O
• Uses: (2R,3S)-3-Hydroxynorleucine is an analogue of DL-6-Hydroxy Norleucine (H948855) which is an intermediate for antiviral and antihypertensive drugs.

Technology Process of (2r,3s)-2-amino-3-hydroxyhexanoic Acid

There total 15 articles about (2r,3s)-2-amino-3-hydroxyhexanoic 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:

(5S,6R)-3-(1-Hydroxy-butyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (129274-25-5) → L-erythro β-Hydroxynorleucine (2076-44-0,2076-55-3,10148-68-2,10148-69-3,34042-01-8,50730-80-8,52773-82-7,59286-25-8,59286-26-9,87585-08-8)

Guidance literature:

With hydrogen; palladium dichloride; In tetrahydrofuran; ethanol; under 2068.6 Torr;

DOI:10.1016/S0040-4039(00)94638-0

Reference yield:

anti-2-bromo-3-hydroxyhexanoic acid → (+/-)-erythro-2-amino-3-hydroxy-hexanoic acid (2076-44-0,2076-55-3,10148-68-2,10148-69-3,34042-01-8,50730-80-8,52773-82-7,59286-25-8,59286-26-9,87585-08-8)

Guidance literature:

With ammonia; water;

Reference yield:

(+/-)-erythro-2-amino-3-hydroxy-hexanoic acid (2076-44-0,2076-55-3,10148-68-2,10148-69-3,34042-01-8,50730-80-8,52773-82-7,59286-25-8,59286-26-9,87585-08-8) → (+/-)-threo-2-amino-3-hydroxy-hexanoic acid (2076-44-0,2076-55-3,10148-68-2,10148-69-3,34042-01-8,50730-80-8,52773-82-7,59286-25-8,59286-26-9,87585-08-8)

Guidance literature:

With thionyl chloride; und Erhitzen des Reaktionsprodukts mit wss.HBr;

upstream raw materials:

(+/-)-erythro-2-amino-3-hydroxy-hexanoic acid

copper(II) glycinate

butyraldehyde

(E)-2-Hexenoic acid

Downstream raw materials:

(+/-)-threo-3-hydroxy-2-(4-nitro-benzoylamino)-hexanoic acid

(+/-)-threo-2-amino-3-hydroxy-hexanoic acid

(+/-)-erythro-3-hydroxy-2-(4-nitro-benzoylamino)-hexanoic acid

(+/-)-erythro-3-hydroxy-2-(toluene-4-sulfonylamino)-hexanoic acid

Refernces

• 1、 Ariyoshi,Yasuda Yamatani. "The structure taste relationships of the dipeptide esters composed of L aspartic acid and β hydroxy amino acids". . p. 326 - 330. Retrieved 2007/10/05.