Category: 617-55-0

Saito, Seiki; Hasegawa, Takashi; Inaba, Masami; Nishida, Ryosuke; Fujii, Toshikazu; Nomizu, Seiya; Moriwake, Toshio published the artcile< Combination of borane-dimethyl sulfide complex with catalytic sodium tetrahydroborate as a selective reducing agent for α-hydroxy esters. Versatile chiral building block from (S)-(-)-malic acid>, Recommanded Product: (S)-Dimethyl 2-hydroxysuccinate, the main research area is butanoate dihydroxy preparation lactonization; borane sulfide reduction malate; borohydride dimethyl sulfide reductant; hydroxy ester selective reduction; butanolide hydroxy; butanal dihydroxy isopropylidene ketal.

BH3-Me2S complex in combination with NaBH4 is an efficient and selective reducing agent for α-hydroxy esters. Thus, reduction of di-Me (S)-(-)-malate with this agent afforded 80% (S)-HOCH2CH(OH)CH2CO2Me, which was converted into chiral building blocks I and II.

Chemistry Letters published new progress about Hydroxy esters Role: RCT (Reactant), RACT (Reactant or Reagent). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Recommanded Product: (S)-Dimethyl 2-hydroxysuccinate.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Mori, Kenji; Ikunaka, Masaya published the artcile< Pheromone synthesis. 65. Synthesis of all of the four energetically possible stereoisomers of 7-ethyl-2-methyl-1,6-dioxaspiro[4.5]decane. A pheromone produced by bees Paravespura vulgaris L. and Andrena haemorrhoa F>, Related Products of 617-55-0, the main research area is dioxaspirodecane ethylmethyl isomer preparation; pheromone ethymethyldioxaspirodecane isomer preparation.

All 4 energetically possible stereoisomers [(2R,5R,7R)-, (2R,5S,7S)-, (2S,5R,7R)- and (2S,5S,7S)] of 7-ethyl-2-methyl-1,6-dioxaspiro[4.5]decane were synthesized from Et (S)-lactate and di-Me (S)-malate or Me (R)-β-hydroxyvalerate employing dianion alkylation as the key-step.

Tetrahedron published new progress about Plant pheromones Role: SPN (Synthetic Preparation), PREP (Preparation). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Related Products of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Nilsson, Jonas W.; Kvarnstroem, Ingemar; Musil, Djordje; Nilsson, Ingemar; Samulesson, Bertil published the artcile< Synthesis and SAR of Thrombin Inhibitors Incorporating a Novel 4-Amino-Morpholinone Scaffold: Analysis of X-ray Crystal Structure of Enzyme Inhibitor Complex>, Quality Control of 617-55-0, the main research area is amino morpholinone scaffold preparation thrombin inhibition crystal; structure activity relationship amino morpholinone scaffold thrombin inhibitor.

A 4-amino-2-carboxymethyl-3-morpholinone structural motif derived from malic acid has been used to mimic D-Phe-Pro in the thrombin inhibiting tripeptide D-Phe-Pro-Arg. The arginine in D-Phe-Pro-Arg was replaced by the more rigid P1 truncated p-amidinobenzylamine (Pab). These new thrombin inhibitors were used to probe the inhibitor binding site of α-thrombin. The best candidate in this series of thrombin inhibitors exhibits an in vitro IC50 of 0.130 μM. Interestingly, the stereochem. of the 4-amino-2-carboxymethyl-3-morpholinone motif is reversed for the most active compounds compared to that of a previously reported 2-carboxymethyl-3-morpholinone series. The X-ray crystal structure of the lead inhibitor cocrystd. with α-thrombin is discussed.

Journal of Medicinal Chemistry published new progress about Crystal structure. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Quality Control of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Orita, Akihiro; Tanahashi, Chiaki; Kakuda, Atsushi; Otera, Junzo published the artcile< Highly Powerful and Practical Acylation of Alcohols with Acid Anhydride Catalyzed by Bi(OTf)3>, Recommanded Product: (S)-Dimethyl 2-hydroxysuccinate, the main research area is alc acylation anhydride bismuth triflate catalyst.

Bi(OTf)3-catalyzed acylation of alcs. with acid anhydride was evaluated in comparison with other acylation methods. The Bi(OTf)3-acid anhydride protocol was so powerful that sterically demanding or tertiary alcs. could be acylated smoothly. Less reactive acylation reagents such as benzoic and pivalic anhydride are also activated by this catalysis. In these cases, a new technol. was developed in order to overcome difficulty in separation of the acylated product from the remaining acylating reagent: methanolysis of the unreacted anhydride into easily separable Me ester realized quite easy separation of the desired acylation product. The Bi(OTf)3-acid anhydride protocol was applicable to a wide spectrum of alcs. bearing various functionalities. Acid-labile THP- or TBS-protected alc., furfuryl alc., and geraniol could be acylated as well as base-labile alcs. Even acylation of functionalized tertiary alcs. was effected at room temperature

Journal of Organic Chemistry published new progress about Acylation. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Recommanded Product: (S)-Dimethyl 2-hydroxysuccinate.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Pattenden, Gerald; Critcher, Douglas J.; Remuinan, Modesto published the artcile< Total synthesis of (-)-pateamine A, a novel immunosuppressive agent from Mycale sp>, Safety of (S)-Dimethyl 2-hydroxysuccinate, the main research area is asym synthesis pateamine A Stille coupling reaction; sulfinimine chiral auxiliary beta amino ester preparation pateamine A.

A convergent synthesis of the unique thiazole-containing polyene bis-lactone pateamine A (I) isolated from the marine sponge Mycale sp is described. The synthesis features the ubiquitous Stille sp2-sp2 coupling reaction to elaborate the E,Z-diene macrolide core and the all-E polyenamine side chain in the natural product. It also highlights the scope for enantiopure sulfinimine intermediates in the synthesis of chiral β-amino ester moieties in complex structures.

Canadian Journal of Chemistry published new progress about Chiral auxiliary. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Safety of (S)-Dimethyl 2-hydroxysuccinate.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Takano, Seiichi; Iwabuchi, Yoshiharu; Ogasawara, Kunio published the artcile< The Katsuki-Sharpless asymmetric epoxidation of (E)-2,5-dihydroxy-2,5-dimethyl-3-hexene>, Electric Literature of 617-55-0, the main research area is asym epoxidation tertiary allylic alc; Katsuki Sharpless epoxidation dihydroxydimethylhexene; absolute configuration epoxydihydroxydimethylhexane.

The first asym. epoxidation of a tertiary allylic alc. by the Katsuki-Sharpless reaction has been demonstrated using (E)-Me2C(OH)CH:CHCMe2OH as a tertiary allylic alc. substrate to afford optically active epoxide I. In 70% ee in an excellent chem. yield.

Tetrahedron Letters published new progress about Absolute configuration. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Electric Literature of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Graham, David E.; Graupner, Marion; Xu, Huimin; White, Robert H. published the artcile< Identification of coenzyme M biosynthetic 2-phosphosulfolactate phosphatase. A member of a new class of Mg2+-dependent acid phosphatases>, Formula: C6H10O5, the main research area is protein sequence Methanococcus gene comB ORF MJ1140 phosphosulfolactate phosphatase; coenzyme M biosynthetic enzyme phylogeny phosphoglycolate phosphatase substrate transphosphorylation.

Coenzyme M (CoM; 2-mercaptoethanesulfonic acid) is the terminal Me carrier in methanogenesis. Methanogenic archaea begin the production of this essential cofactor by sulfonating phosphoenolpyruvate to form 2-phospho-3-sulfolactate. After dephosphorylation, this precursor is oxidized, decarboxylated and then reductively thiolated to form CoM. A thermostable phosphosulfolactate phosphohydrolase (EC 3.1.3.-) catalyzing the second step in CoM biosynthesis, was identified in the hyperthermophilic euryarchaeon Methanococcus jannaschii. The predicted ORF MJ1140 in the genome of M. jannaschii encodes ComB, a Mg2+-dependent acid phosphatase that is specific for 2-hydroxycarboxylic acid phosphatase esters. Recombinantly expressed purified ComB efficiently hydrolyzes rac-2-phosphosulfolactate, (S)-2-phospholactate, phosphoglycolate and both enantiomers of 2-phosphomalate. In contrast to previously studied phosphoglycolate phosphatases, ComB has a low pH optimum for activity, a narrow substrate specificity and an amino acid sequence dissimilar to any biochem. characterized protein. Like other phosphatases that function via covalent phosphoenzyme intermediates, ComB can catalyze a transphosphorylation reaction. Homologs of comB are identified in all available cyanobacterial genome sequences and in genomes from phylogenetically diverse bacteria and archaea; most of these organisms lack homologs of other CoM biosynthetic genes. The broad and disparate distribution of comB homologs suggests that the gene has been recruited frequently into new metabolic pathways.

European Journal of Biochemistry published new progress about Divalent cations. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Formula: C6H10O5.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Booth, Paul M.; Fox, Christina M. J.; Ley, Steven V. published the artcile< Preparation of acyltetronic acids using tert-butyl acetothioacetate: total synthesis of the fungal metabolites carolic, carlosic, and carlic acids>, Application In Synthesis of 617-55-0, the main research area is carolate total synthesis; carlosate total synthesis; carlate total synthesis; acetothioacetate dianion alkylation; oxoalkanethioate preparation transesterification; oxoacyloxylalkanoate preparation ring closure.

Dianions of MeCOCH2C(O)SCMe3 were allylated with a variety of electrophiles at the γ-C. Treatment of the products with 2-hydroxy esters in the presence of Ag (I) salts gave transesterified acetoacetate derivs in good yields. These acetoacetates were cyclized to acyltetronic acid derivs using Bu4NF in THF at room temperature Natural products carlosic (I) carolic (II; R = Me) and carlic acids (II; R = CH2CO2H) acids were prepared this way.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about Cyclization. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Application In Synthesis of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Falck, J. R.; Sun, Lumin; Lee, Sang Gyeong; Heckmann, Bertrand; Mioskowski, Charles; Karara, Armando; Capdevila, Jorge published the artcile< Enantiospecific synthesis of 17- and 18-hydroxyeicosatetraenoic acids, cytochrome P450 arachidonate metabolites>, Synthetic Route of 617-55-0, the main research area is hydroxyeicosatetraenoate stereoselective preparation; eicosatetraenoate hydroxy stereoselective preparation; cuprate addition bromobutanediol tosylate.

The title bioactive eicosanoids were prepared from di-Me L-malate by a convergent strategy exploiting the differential reactivity of ethereal dialkylcuprates towards tosylate vs. bromide in the intermediate I.

Tetrahedron Letters published new progress about Addition reaction, regioselective. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Synthetic Route of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Sheppard, George S. published the artcile< Copper(II) pivalate/oxone. An improved promoter system for aryl transfer via organo-bismuth reagents>, Formula: C6H10O5, the main research area is aromatic ether preparation; alc arylbismuth arylation copper pivalate catalyst.

Effective conditions for the arylation of OH groups prone to elimination are reported. Modest success was achieved using triarylbismuth reagents under literature conditions. Based on the side-products observed in the reaction, the oxidant used for in-situ oxidation of Bi(III) to Bi(V) and the Cu salt used as promoter were modified. These changes led to substantially improved results.

Synlett published new progress about Aromatic ethers Role: SPN (Synthetic Preparation), PREP (Preparation). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Formula: C6H10O5.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics