114819-44-2

Upstream product

• 81028-03-7 (Z)-4-benzyloxy-but-2-en-1-ol 
• 497-06-3 3,4-butenediol 
• 100-39-0 benzyl bromide 
• 93553-66-3 1-(benzyloxy)but-3-en-2-ol 
• 114826-50-5 (4R,5S)-2,2-dimethyl-4-iodomethyl-5-benzyloxymethyl-1,3-dioxolane 
• 113426-92-9 benzyloxy-1 epoxy-2R,3S iodo-4 butane 
• 119046-51-4 (2S,3S,4S)-1-O-benzyl-3,4-epoxy-4-(trimethylsilyl)butane-1,2-diol 
• 117821-04-2 (R)-4-Benzyloxy-3-hydroxybutyl methyl sulfoxide 
• 113426-91-8 cis-4-benzyloxy-2,3-epoxybutyl tosylate 
• 108-05-4 vinyl acetate 
• 1030268-21-3 trimethylsulfonium iodide 
• 14618-80-5 (R)-benzyl glycidol 
• 233670-05-8 (R)-1-(benzyloxy)but-3-en-2-yl acetate 
• 200205-69-2 Toluene-4-sulfonic acid (2R,3R)-3-benzyloxymethyl-oxiranylmethyl ester 

Downstream Products

• 142204-63-5 (2S)-3-benzoyloxy-4-benzyloxy-1-butene 
• 661490-54-6 ((R)-1-Benzyloxymethyl-allyloxy)-acetic acid 
• 638165-80-7 C₂₅H₃₈N₂O₇S 
• 887143-90-0 (E)-(R)-1-Benzyloxy-4-((1R,6R,8R)-1-oxo-2,9,10-trioxa-1λ⁵-phospha-bicyclo[4.3.1]dec-4-en-8-yl)-but-3-en-2-ol 
• 1000045-23-7 (1R)-3-methylbutanoic acid 1-[(benzyloxy)methyl]prop-2-en-1-yl ester 
• 661490-74-0 (S)-3-[(R)-2-((R)-1-Benzyloxymethyl-allyloxy)-4-methoxymethoxy-pent-4-enoyl]-4-isopropyl-oxazolidin-2-one 
• 661490-75-1 (R)-3-[(S)-2-((R)-1-Benzyloxymethyl-allyloxy)-4-methoxymethoxy-pent-4-enoyl]-4-isopropyl-oxazolidin-2-one 
• 661490-78-4 (S)-3-((2R,6R)-6-Benzyloxymethyl-4-methoxymethoxy-3,6-dihydro-2H-pyran-2-carbonyl)-4-isopropyl-oxazolidin-2-one 
• 661490-79-5 (R)-3-((2S,6R)-6-Benzyloxymethyl-4-methoxymethoxy-3,6-dihydro-2H-pyran-2-carbonyl)-4-isopropyl-oxazolidin-2-one 
• 638165-81-8 2-(2S)-[(6S)-(6-benzyloxymethyl-7-(1,1-dimethylethoxy)carbonyl-1,1-dioxo-2,3,6,7-tetrahydro-1,2,7-thiadiazepin-2-yl)]-3-methyl-butyric acid methyl ester 
• 661490-62-6 (R)-3-[2-((R)-1-Benzyloxymethyl-allyloxy)-acetyl]-4-isopropyl-oxazolidin-2-one 
• 661490-60-4 (S)-3-[2-((R)-1-Benzyloxymethyl-allyloxy)-acetyl]-4-isopropyl-oxazolidin-2-one 

Relevant academic research and scientific papers

Stereoselective photochemical 1,3-dioxolane addition to 5-alkoxymethyl-2(5H)-furanone: Synthesis of bis-tetrahydrofuranyl ligand for HIV protease inhibitor UIC-94017 (TMC-114)

A convenient synthesis of (3R,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan, a high-affinity non-peptidal ligand for HIV protease inhibitor UIC-94017, is described. This inhibitor is undergoing advanced clinical trials. The synthesis utilizes a novel stereoselective photochemical 1,3-dioxolane addition to 5(S)-benzyloxymethyl-2(5H)-furanone as the key step. The requisite furanone derivative was prepared in high enantiomeric excess by an immobilized lipase-catalyzed selective acylation of (±)-1-(benzyloxy)-3-buten-2-ol and a ring-closing olefin metathesis with Grubbs' catalyst. Optically active bis-THF was converted to protease inhibitor 2 (UIC-94017).

Total Synthesis of the Echinodermatous Ganglioside LLG-3 Possessing the Biological Function of Promoting the Neurite Outgrowth

A total synthesis of echinodermatous ganglioside LLG-3 with neuritogenic activity was accomplished by a convergent strategy. The synthesis of 2-hydroxyethyl 8-O-Me-α-sialoside 2 was started from the phenyl 7,8-di-O-Pico-thiosialoside 5, which can be chemoselectively removed the picoloyl group, and then the methyl group in 8-O-MeNeu5Ac moiety was chemoselectively prepared using TMSCHN2/FeCl3. For preparation of the terminal disialic unit, oxidative amidation was initially utilized by our group to efficiently construct the α(2,11) linkage of 8-O-Me-Neu5Acα(2,11)Neu5Gc. Herein, we also demonstrate that the synthesized ganglioside LLG-3 exhibited the neuritogenic activity toward the primary cortical neurons and that biological activity is superior to that of ganglioside DSG-A.

Regio- and stereoretentive synthesis of branched, linear (E)- and (Z)-allyl fluorides from allyl carbonates under Ir-catalysis

This paper describes a new catalytic method for the regio- and stereocontrolled fluorination of allylic carbonates. This transformation uses TBAF·4tBuOH as the fluoride source and [Ir(COD)Cl]2 as the catalyst; the most commonly used [Ir(COD)Cl]2/phosphoramidite system is ineffective. Synthetically, this reaction is characterized by a high degree of structural conservation in going from substrates to the products. The fluorination of (E)-allylic carbonates leading to linear (E)-allylic fluorides (l : b > 20 : 1, E : Z > 20 : 1) is unprecedented and a unique feature of fluoride as the nucleophile. The first examples of transition metal catalyzed fluorination affording (Z)-allyl fluorides (Z : E ratio >20 : 1) are disclosed along with the successful fluorination of branched, linear (E)- and (Z)-allyl carbonates with [18F] fluoride in the presence of [Ir(COD)Cl]2. 18O-Labeling of the reactant reveals internal return during the allylic ionization step, and pathways for effective intra- and intermolecular isotope exchange.

Enantioselective synthesis of possible diastereomers of heptadeca-1-ene-4,6-diyne-3,8,9,10-tetrol; Putative structure of a conjugated diyne natural product isolated from hydrocotyle leucocephala

Enantioselective synthesis of possible diastereomers of heptadeca-1-ene-4,6-diyne-3,8,9,10-tetrol, a structure proposed for the natural product isolated from Hydrocotyle leucocephala is accomplished. The reported spectral data of the natural product did n

CYCLIC AMINE COMPOUND

The present invention provides an excellent antihypertensive medicament. The medicament of the present invention comprises a compound having the general formula (I) and the like: [wherein R1: H, substitutable alkyl, substitutable alkenyl, substitutable cyclic hydrocarbon, substitutable heterocyclyl or the like; R2: H, substitutable alkyl, substitutable alkenyl, substitutable cycloalkyl or the like; R3, R4; H, substitutable alkyl, substitutable alkenyl, substitutable cycloalkyl or the like; R5, R6: H, substitutable alkyl, substitutable cycloalkyl, substitutable alkoxy or the like; R7, R8: H, substitutable alkyl, substitutable cycloalkyl or the like; X: the formula (II) or the like; A: substitutable cyclic hydrocarbon, substitutable heterocyclyl or the like; Y: a single bond, substitutable alkylene, substitutable alkenylene, -(CH2)a-X1-(CH2)b- (X1: the formula -NH-, -O- or the like; a, b: 0-5) or the like; B: substitutable cyclic hydrocarbon, substitutable heterocyclyl or the like].

METHOD OF PREPARING (3R, 3aS, 6aR) -3- HYDROXYHEXAHYDROFURO [2, 3-b] FURAN AND RELATED COMPOUNDS

A method of synthesizing (3R, 3aS, 6aR) -3- hydroxyhexahydrofuro [2, 3-b] furan (I), and related compounds, in high yield and high enantiomeric selectivity is disclosed. Also disclosed is a method of manufacturing (5S) -5-(benzyloxymethyl) -5H-furan-2-one.

Enantioselective total synthesis of (+)-gigantecin: Exploiting the asymmetric glycolate aldol reaction

The enantioselective synthesis of the potent, selective, cytotoxic, annonaceous acetogenin, (+)-gigantecin, has been completed. An asymmetric glycolate aldol serves to establish the stereocenters at C13,14 and at C21,22. A Carreira asymmetric acetylide ad

A unified approach to the enantioselective synthesis of 2,6-cis and trans disubstituted tetrahydropyranones

A stereoselective construction of cis- and trans-2,6-disubstituted tetrahydropyranones, based on strategy which combines an asymmetric alkylation and ring closing metathesis for the formation of a cyclic enol ether, is reported.

Ultrasound-accelerated synthesis of chiral allylic alcohols promoted by indium metal

The 2-iodomethyl-O-isopropylidine acetals undergo smoothly β-elimination by indium metal in methanol under sonication to afford the corresponding allylic alcohols in excellent yields with high selectivity. This method tolerates both acid and base labile functional and protecting groups and also free hydroxyl groups present in the molecule. Improved yields and enhanced rates are the remarkable features obtained by ultrasound.

New synthesis of sn-1,2- and sn-2,3-O-diacylglycerols application to the synthesis of enantiopure phosphonates analogous to triglycerides: A new class of inhibitors of lipases

Phosphonate compounds mimic the first transition state occurring during enzymatic carboxyester hydrolysis of natural substrates by forming a covalent bond with the catalytic serine. However, until now the organophosphorus compounds used in the inhibition studies more or less resembled a natural triglyceride substrate. In order to elucidate the interfacial activation and the mechanism of action of lipases, specific inhibitors need to be prepared. To achieve this goal, enantiomerically pure sn-1,2- and sn-2,3O- didecanoylglycerol compounds were prepared - starting from a C-4 chiral synthon, 3-buten-1,2-diol - and treated with n-pentylphosphonic dichloride and p-nitrophenol to afford the corresponding diastereomeric phosphonates, which were acylglycerol analogs. Subsequent separation of each of the phosphonate diastereomers A/B or ent-A/ent-B, performed by HPLC, led to four enantiopure stereoisomers that will be investigated as inhibitors of Human Pancreatic Lipase (HPL) and Human Gastric Lipase (HGL) using the monomolecular film technique.