34695-32-4

Usage

Chemical Properties

Off-White Solid

InChI:InChI=1/C6H8O4/c1-6(9)2-4(7)10-5(8)3-6/h9H,2-3H2,1H3

Upstream product

• 503-49-1 meglutol 
• 16649-49-3 Acetic anhydride-d6 
• 25201-40-5 1,1-diallylethanol 

Downstream Products

• 1553-55-5 DL-3-hydroxy-3-methylglutaryl coenzyme A 
• 480-87-5 (+)-dicrotaline 
• 81969-90-6 13-epi-dicrotaline 
• 674-26-0 mevalonolactone 
• 6158-93-6 [5,5-2H2]mevalonic acid lactone 
• 6247-73-0 S-(4-carboxy-3-methyl-but-2ξ-enoyl)-coenzyme-A 
• 503-49-1 meglutol 
• 69172-23-2 5H-r,trans-3-hydroxy-cis-3-methyl-7-phenylheptan-5-olide 
• 69172-23-2 5H-r,cis-3-hydroxy-trans-3-methyl-7-phenylheptan-5-olide 
• 946831-51-2 (3R)-1-[(S)-1-phenylethyl]mevalonamide 
• 176755-40-1 (S)-4-Cyclohexylcarbamoyl-3-hydroxy-3-methyl-butyric acid methyl ester 

Relevant academic research and scientific papers

Control of β-Branching in Kalimantacin Biosynthesis: Application of 13C NMR to Polyketide Programming

The presence of β-branches in the structure of polyketides that possess potent biological activity underpins the widespread importance of this structural feature. Kalimantacin is a polyketide antibiotic with selective activity against staphylococci, and its biosynthesis involves the unprecedented incorporation of three different and sequential β-branching modifications. We use purified single and multi-domain enzyme components of the kalimantacin biosynthetic machinery to address in vitro how the pattern of β-branching in kalimantacin is controlled. Robust discrimination of enzyme products required the development of a generalisable assay that takes advantage of 13C NMR of a single 13C label incorporated into key biosynthetic mimics combined with favourable dynamic properties of an acyl carrier protein. We report a previously unassigned modular enoyl-CoA hydratase (mECH) domain and the assembly of enzyme constructs and cascades that are able to generate each specific β-branch.

A new reagent for the preparation of chiral HMGA (3-hydroxy-3-methylglutaric acid) esters and amides. Synthesis of (R)- and (S) -β-carboxymethyl-β-methyl-β-lactones by asymmetric desymmetrization of HMGA anhydride

(R)- and (S)-βarboxymethyl-β-methyl-β-lactones, new reagents for the preparation of chiral HMGA (3-hydroxy-3-methylglutaric acid) esters and amides were developed through the asymmetric desymmetrization of HMGA anhydride. The reagent was smoothly reactedwith various alkoxide without racemization to afford the desirable half-esters. On the other hand, the reaction with various amine in refluxing toluene gave a racemic amide. The chiral HMGA amide was prepared using the corresponding methyl ester of the reagent.

Studies on a Synthesis of (RS)-Mevalonic Acid Lactone

Full details of a high yielding synthesis of mevalonic acid lactone (1) which is of particular value in the preparation of 3- and/or 3'-labelled compounds are described.The key step, conversion of 3-hydroxy-3-methylpentane-1,5-dioic acid (3) into 3-hydroxy-3-methylpentane-1,5-dioic anhydride (4) using acetic anhydride, has been fully investigated, and an additional method using acetyl chloride and triethylamine is described.

Reinvestigation of a Synthesis of (R,S)-Mevalonolactone

An n.m.r. study of the reaction of 3-hydroxy-3-methylpentane-1,5-dioic acid (5) with excess of acetic anhydride is described.It has shown that 3-hydroxy-3-methylpentane-1,5-dioic acid anhydride (2), previously described by Scott and Shishido as an intermediate in their synthesis of mevalonolactone, is formed only transiently, along with 3-acetoxy-3-methylpentane-1,5-dioic acid (6).Both intermediates eventually give 3-acetoxy-3-methylpentane-1,5-dioic acid anhydride (3).To obtain (R,S)-mevalonolactone, sodium borohydride reduction of 3-hydroxy-3-methylpentane-1,5-dioic acid anhydride (2), prepared from the diacid (5) and N,N-dicyclohexylcarbodi-imide, is shown to be better than reduction of 3-acetoxy-3-methylpentane-1,5-dioic acid anhydride (3).

Macrocyclic Pyrrolizidine Alkaloids. Synthesis and Stereochemistry of (+)-Dicrotaline (13β-Hydroxy-13α-methyl-1,2-didehydrocrotalanine) and (+)-13-epi-Dicrotaline

Treatment of (+)-retronecine (1) with the trimethylsilyl ether of 3-hydroxy-3-methylglutaric anhydride gave a mixture of the 7- and 9-monoesters of (+)-retronecine (1).Lactonisation of this mixture was achieved using the corresponding pyridine-2-thiol esters to give (+)-dicrotaline (13β-hydroxy-13α-methyl-1,2-didehydrocrotalanine) (2) and (+)-13-epi-dicrotaline (3).The absolute configuration at C-13 in both compounds was established by a sequence of selective reactions on each epimer to yield optically active mevalonolactone.

An Easy Synthesis of (RS)-Mevalonic Acid Lactone

A high-yielding synthesis of mevalonic acid lactone is described which is of particular value in the preparation of 3' labelled compounds.