56577-28-7

Basic information

• Product Name: Pentanoic acid, 2-hydroxy-3-methyl-, methyl ester, (2S,3S)-
• Synonyms: (2S,3S)-2-Hydroxy-3-methyl-pentanoic acid methyl ester;methyl 2-hydroxy-3-methylpentanoate;(2S,3S)-2-hydroxy-3-methylpentanoic acid methyl ester;methyl (2S,3S)-2-Hydroxy-3-methylpentanoate
• CAS NO: 56577-28-7
• Molecular Formula: C7H14O3
• Molecular Weight: 146.186
• Mol File: 56577-28-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 82-83 °C(Press: 17 Torr)
• Density: 1.002±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Pentanoic acid, 2-hydroxy-3-methyl-, methyl ester, (2S,3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pentanoic acid, 2-hydroxy-3-methyl-, methyl ester, (2S,3S)-(56577-28-7)
• EPA Substance Registry System: Pentanoic acid, 2-hydroxy-3-methyl-, methyl ester, (2S,3S)-(56577-28-7)

Safety Data

• Hazardous Substances Data: 56577-28-7(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 32513-91-0 (3S)-2-Acetoxy-3-methylvaleric acid 
• 71215-25-3 2-Hydroxy-3-methyl-pent-4-enoic acid methyl ester 

Downstream Products

• 132149-75-8 (4R,5R)-4-sec-Butyl-2-oxo-5-phenylsulfanyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 132149-84-9 ((1R,2S)-2-Methyl-1-phenylsulfanylmethyl-butyl)-carbamic acid tert-butyl ester 
• 118656-50-1 5-phenylthiooxazolidin-2-one 
• 132149-83-8 ((1R,2S)-1-Benzyloxymethyl-2-methyl-butyl)-carbamic acid tert-butyl ester 
• 132149-82-7 ((2S,3S)-2-Methoxymethoxy-3-methyl-pentyloxymethyl)-benzene 
• 106946-74-1 Boc-D-allo-isoleucinol 
• 159360-04-0 (4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid methyl ester 
• 159407-39-3 (3S,4R,5S)-4-benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid methyl ester 
• 13139-16-7 N-tert-butoxycarbonyl-D-alloisoleucine 
• 3160-59-6 N-benzyloxycarbonylamino-D-alloisoleucine 
• 54831-20-8 (2R,3S)-2-acetamido-3-methylpentanoic acid 
• 1509-35-9 D-alloisoleucine 
• 188775-06-6 (4R,5S)-4-Dibenzylamino-5-methyl-3-oxo-heptanoic acid tert-butyl ester 
• 188774-94-9 (2R,3S)-2-Dibenzylamino-3-methyl-pentanoic acid 

Relevant articles and documents

General and efficient α-oxygenation of carbonyl compounds by TEMPO induced by single-electron-transfer oxidation of their enolates

A generally applicable method for the synthesis of protected α-oxygenated carbonyl compounds is reported. It is based on the single-electron-transfer oxidation of easily generated enolates to the corresponding α-carbonyl radicals. Coupling with the stable free radical TEMPO provides α-(piperidinyloxy) ketones, esters, amides, acids or nitriles in moderate-to-excellent yields. Enolate aggregates influence the outcome of the oxygenation reactions significantly. Competitive reactions have been analyzed and conditions for their minimization are presented. Chemoselective reduction of the products led to either N-O bond cleavage to α-hydroxy carbonyl compounds or reduction of the carbonyl functionality tomonoprotected 1,2-diols or O-protected amino alcohols. The oxygenation of enolates proves to be the most general and effective methodology for the synthesis of O-protected α-oxy carbonyl compounds and nitriles A. The scope and limitations of the electron-transfer-induced radical coupling reaction with TEMPO are presented. The reaction pathways are outlined. Methods for the deprotection to α-hydroxy carbonyl compounds B are provided and discussed. Copyright

ASYMMETRIC WITTIG SIGMATROPIC REARRANGEMENT INVOLVING A CHIRAL AZAENOLATE AS THE MIGRATING TERMINUS. A SIMPLE SYNTHESIS OF (+)-VERRUCARINOLACTONE

The diastereo- and/or enantioselection are described in the title rearrangement of the chiral 2-(2-alkenyloxy)methyl 2-oxazolines which eventually provides optically active α-hydroxy γ,δ-unsaturated esters and (+)-verrucarinolactone.