218608-81-2

Basic information

• Product Name: (S)-3-AMINO-5,5-DIMETHYLHEXANOIC ACID
• Synonyms: (S)-3-AMINO-5,5-DIMETHYLHEXANOIC ACID
• CAS NO: 218608-81-2
• Molecular Formula: C8H17NO2
• Molecular Weight: 159.22608
• Mol File: 218608-81-2.mol

Chemical Properties

• Boiling Point: 259.2 °C at 760 mmHg
• Flash Point: 110.6 °C
• Appearance: /
• Density: 0.999 g/cm³
• Vapor Pressure: 0.00396mmHg at 25°C
• Refractive Index: 1.466
• CAS DataBase Reference: (S)-3-AMINO-5,5-DIMETHYLHEXANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-AMINO-5,5-DIMETHYLHEXANOIC ACID(218608-81-2)
• EPA Substance Registry System: (S)-3-AMINO-5,5-DIMETHYLHEXANOIC ACID(218608-81-2)

Safety Data

• Hazardous Substances Data: 218608-81-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H17NO2/c1-8(2,3)5-6(9)4-7(10)11/h6H,4-5,9H2,1-3H3,(H,10,11)/t6-/m1/s1

Upstream product

• 2987-16-8 3,3-dimethylbutyrylaldehyde 
• 1370687-52-7 C₁₅H₂₅NO₄ 
• 1370639-71-6 C₂₇H₄₃NO₉ 
• 147228-25-9 (3R)-ethyl 5,5-dimethyl-3-(tosylamino)hexanoate 
• 147228-31-7 (3R)-5,5-dimethyl-3-(tosylamino)hexanoic acid 

Relevant articles and documents

Enantioselective, chromatography-free synthesis of β3-Amino acids with natural and unnatural side chains

β3-Amino acids are key components of some pharmaceuticals, excellent surrogates for metabolically labile α-amino acids, and building blocks for chiral heterocycles. Unfortunately they are not easily accessible in enantiomerically pure form, especially when possessing unnatural side chains. A flexible, chromatography-free process for the synthesis of enantiopure β3-amino acids possessing natural and unnatural side chains is described. The procedure uses inexpensive starting materials and reagents and offers a good alternative to the hazardous and expensive Arndt-Eistert homologation of enantiopure α-amino acids. Its utility has been demonstrated with the preparative scale synthesis of two valuable β3-amino acids possessing unnatural side chains.

104. The enantioselective synthesis of β-amino acids, their α-hydroxy derivatives, and the N-terminal components of bestatin and microginin

L-Aspartic acid by tosylation, anhydride formation, and reduction with NaBH4 was converted into (3S)-3-(tosylamino)butan-4-olide (8; Scheme 1). Treatment of 8 with ethanolic trimethylsilyl iodide gave the N-protected deoxy-iodo-β-homoserine ethyl ester 9. The latter, on successive nucleophilic displacement with lithium dialkylcuprates (→ 10a-e), alkaline hydrolysis (→ 11a-e), and reductive removal of the tosyl group, produced the corresponding 4-substituted (3R)-3-aminobutanoic acids 12a-e (ee >99%). Electrophilic hydroxylation of 8 (→ 19; Scheme 3), subsequent iodo-esterification (→ 21; Scheme 4), and nucleophilic alkylation and phenylation afforded, after saponification and deprotection, a series of 4-substituted (2S,3A)-3-amino-2-hydroxybutanoic acids 24 including the N-terminal acids 24e (= 3) and 24f (= 4) of bestatin and microginin (de >95%), respectively.

An enantiospecific synthesis of β-amino acids

L-Aspartic acid by regioselective modification of the α-carboxylic acid group, namely N-tosylation, anhydride formation, reduction, iodo-esterification, alkylation, and deprotection afforded a series of γ-alkyl β-aminobutyric acids of the R configuration (ee > 99%).