Tag: M.W=300-350

Raghavan, Sadagopan published the artcileA short convergent synthesis of the [3.2.1]dioxabicyclooctane subunit of sorangicin A via regioselective epoxide opening, Name: (+)-B-Methoxydiisopinocampheylborane, the publication is Tetrahedron (2018), 74(10), 1071-1077, database is CAplus.

In this paper, we disclose the synthesis of the dioxabicyclo[3.2.1]octane subunit (I) of the potent antibiotic sorangicin A. The synthesis was achieved in a convergent manner in 8 steps. Regio- and stereoselective intermol. epoxide opening, ring-closing metathesis and iodo-etherification are key steps. cis-2-Butene diol has been employed as a common staring material.

Tetrahedron published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Name: (+)-B-Methoxydiisopinocampheylborane.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Trost, Barry M. published the artcileTotal Synthesis and Stereochemical Assignment of (-)-Ushikulide A, Safety of (+)-B-Methoxydiisopinocampheylborane, the publication is Journal of the American Chemical Society (2009), 131(41), 15061-15074, database is CAplus and MEDLINE.

We report the determination of the full stereostructure of (-)-ushikulide A (I), a spiroketal containing macrolide by total synthesis. Ushikulide A was isolated from a culture broth of Streptomyces sp. IUK-102 and exhibits potent immunosuppressant activity (IC₅₀ = 70 nM). To embark upon an ushikulide A synthesis, a tentative assignment was made based on analogy to cytovaricin, a related macrolide isolated from a culture of Streptomyces diastatochromogenes whose full structure was previously established via synthesis and X-ray crystallog. This report delineates studies on several key steps, namely a direct aldol reaction catalyzed by the dinuclear zinc ProPhenol complex, a metal catalyzed spiroketalization, as well as application of an unprecedented asym. alkynylation of a simple saturated aldehyde with Me propiolate to prepare the nucleophilic partner for a Marshall-Tamaru propargylation. These studies culminated in the first total synthesis and stereochem. assignment of (-)-ushikulide A and significantly extended the scope of the above-mentioned methodologies.

Journal of the American Chemical Society published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C15H21BO2, Safety of (+)-B-Methoxydiisopinocampheylborane.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Eggen, MariJean published the artcileTotal Synthesis of Cryptophycin-24 (Arenastatin A) Amenable to Structural Modifications in the C16 Side Chain, Formula: C21H37BO, the publication is Journal of Organic Chemistry (2000), 65(23), 7792-7799, database is CAplus and MEDLINE.

Two efficient protocols for the synthesis of tert-Bu (5S,6R,2E,7E)-5-[(tert-butyldimethylsilyl)oxy]-6-methyl-8-phenyl-2,7-octadienoate, a major component of the cryptophycins, are reported. The first utilized the Noyori reduction and Frater alkylation of Me 5-benzyloxy-3-oxopentanoate to set two stereogenic centers, which became the C16 hydroxyl and C1′ Me of the cryptophycins. The second approach started from 3-p-methoxybenzyloxypropanal and a crotyl borane reagent derived from (-)-α-pinene to set both stereocenters in a single step and provided the dephenyl analog, tert-Bu (5S,6R,2E)-5-[(tert-butyldimethylsilyl)oxy]-6-methyl-2,7-octadienoate, in five steps. This compound was readily converted to the 8-Ph compound via Heck coupling. The silanyloxy esters were efficiently deprotected and coupled to the C2-C10 amino acid fragment to provide desepoxyarenastatin A and its dephenyl analog. The terminal olefin of the latter was further elaborated via Heck coupling. Epoxidation provided cryptophycin-24 (arenastatin A).

Journal of Organic Chemistry published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Formula: C21H37BO.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Craviso, Gale L. published the artcileCompetitive inhibition of stereospecific opiate binding by local anesthetics in mouse brain, HPLC of Formula: 637-58-1, the publication is Life Sciences (1975), 16(12), 1803-8, database is CAplus and MEDLINE.

Cationic local anesthetics inhibited competitively the stereospecific binding of naltrexone (I) [16590-41-3] and etorphine [14521-96-1] to the mouse brain opiate receptor. In contrast, the inhibition produced by benzocaine [94-09-7], a noncationic local anesthetic, was noncompetitive. Thus, it appears that the cationic group of local anesthetics interacts with a specific anionic binding site on the opiate receptor and that there are certain structural similarities between the receptors for both types of drugs. In addition, several drugs appear to be able to unspecifically modify the pharmacol. effects of opiates and they could be useful tools to further characterize the opiate receptor.

Life Sciences published new progress about 637-58-1. 637-58-1 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, and the molecular formula is C17H28ClNO3, HPLC of Formula: 637-58-1.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Melnik, Kristina published the artcileIdentification and Synthesis of Luteolide, a Highly Branched Macrolide Semiochemical from the Mantellid Frog Gephyromantis luteus, SDS of cas: 99438-28-5, the publication is Organic Letters (2019), 21(8), 2851-2854, database is CAplus and MEDLINE.

Luteolide is a 10-membered aliphatic macrolactone, (-)-(4R,8S,9S)-4,8-dimethylundecan-9-olide, released by the femoral gland of males of the mantellid frog Gephyromantis luteus. Its structure was established using NMR, MS, and chiral GC and confirmed by stereoselective synthesis of different stereoisomers. Among the approx. 20 current macrolides known from the Mantellidae, luteolide is the first example of a volatile macrolide furnishing three stereogenic centers and an Et side chain.

Organic Letters published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, SDS of cas: 99438-28-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Ramadan, Nesrin K. published the artcileIon-selective electrodes for the potentiometric determination of pramoxine HCl using different ionophores, Computed Properties of 637-58-1, the publication is Acta Chimica Slovenica (2012), 59(4), 870-878, database is CAplus and MEDLINE.

Four novel pramoxine HCl (PAM) selective electrodes were investigated with 2-nitrophenyl octylether as a plasticizer in a polymeric matrix of polyvinyl chloride (PVC). Sensor 1 was fabricated using sodium-tetraphenylborate (TPB) as an anionic exchanger without incorporation of an ionophore. Sensor 2 used 2-hydroxy propyl-cyclodextrin as an ionophore, while sensors 3 and 4 were constructed using 4-sulfocalix-6-arene and 4-sulfocalix-8-arene, resp. as ionophores. Linear responses of PAM within the concentration ranges of 1.0 × 10^-4 to 1.0 × 10^-2 mol L^-1 and 1.0 × 10^-5 to 1.0 × 10^-2 mol L^-1 were obtained using sensors 1 and 2, resp. and 1.0 × 10^-6 to 1.0 × 10^-2 mol L^-1 were obtained using sensors 3 and 4. Nernstian slopes of 50.4, 54.3, 56.3, and 59.1 mV/decade over the pH range of 3.0-6.0 were observed The selectivity coefficients of the developed sensors indicated excellent selectivity for PAM. The utility of 2-hydroxy-Pr β-cyclodextrin (2HP-β-CD) and 4-sulfocalix [6,8] arene (SC 6,8) as ionophores had a significant influence on increasing the membrane sensitivity and selectivity of sensors 2, 3, and 4 compared to sensor 1. The proposed sensors displayed useful anal. characteristics for the determination of PAM in bulk powder, pharmaceutical formulation, and in biol. fluid. Validation of the method showed the suitability of the proposed electrodes for the use in the quality control assessment of the drug. Furthermore, statistical comparison between the results obtained by the proposed method and the official method of the drug was performed and no significant difference was found.

Acta Chimica Slovenica published new progress about 637-58-1. 637-58-1 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, and the molecular formula is C17H28ClNO3, Computed Properties of 637-58-1.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Merey, Hanan A. published the artcileSimultaneous determination of pramocaine HCl and hydrocortisone acetate in pharmaceutical dosage form, Category: ethers-buliding-blocks, the publication is Journal of Liquid Chromatography & Related Technologies (2013), 36(19), 2774-2784, database is CAplus.

Two sensitive and selective methods were developed and validated for simultaneous determination of pramocaine HCl and hydrocortisone acetate in pharmaceutical dosage form. The first method is a spectrodensitometric method where pramocaine HCl and hydrocortisone acetate were separated using toluene:methanol:chloroform: 10% NH₃ [(5:3:6:0.1, by volume) as the developing system followed by densitometric measurement at 290 nm] and 250 nm for pramocaine HCl and hydrocortisone acetate, resp. The second method is a high performance liquid chromatog. method for separation and determination of both drugs using reversed phase C₁₈ column and mobile phase consisting of distilled water:acetonitrile:triethylamine (530:470:0.1, by volume); pH was adjusted to 3 by o-phosphoric acid. The proposed methods were successfully applied for the anal. of pramocaine HCl and hydrocortisone acetate in laboratory prepared mixtures and in pharmaceutical dosage form and the results obtained were assessed by applying the standard addition technique. Statistical comparison between the results obtained by applying the proposed methods and official method for the cited drugs was done and no significant difference was found at p = 0.05.

Journal of Liquid Chromatography & Related Technologies published new progress about 637-58-1. 637-58-1 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, and the molecular formula is C17H28ClNO3, Category: ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Bury, Ross W. published the artcileInteractions between local anesthetics and spasmogens on the guinea-pig ileum, Safety of 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, the publication is Journal of Pharmacology and Experimental Therapeutics (1976), 197(3), 633-40, database is CAplus and MEDLINE.

The effect of various local anesthetics and other substances known to modify Ca fluxes in cells, on submax. responses of guinea pig ileum to substance P [33507-63-0], acetylcholine, histamine, and BaCl2 was determined Procaine-HCl [51-05-8] caused a dose-related depression of the response to all the agonists but the response to substance P was far less susceptible to this depression. Lidocaine-HCl [73-78-9], bupivacaine-HCl [18010-40-7], pramoxine-HCl [637-58-1] and W 6211 [22759-46-2] also caused a lower degree of attenuation of the response to substance P than the responses to acetylcholine, histamine, and BaCl2. Verapamil [52-53-9] caused a dose-related depression of responses to all the agonists equally. The use of Ca-free solutions abolished responses to substance P, acetylcholine, and histamine. The response to BaCl2 was less affected by Ca withdrawal but was reduced markedly. In the presence of 10 mM LaCl, the response to all the agonists was abolished. The relative resistance of the substance P responses to antagonism by local anesthetics suggests that different and more efficient channels for Ca entry into the smooth muscle cell are involved.

Journal of Pharmacology and Experimental Therapeutics published new progress about 637-58-1. 637-58-1 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, and the molecular formula is C17H28ClNO3, Safety of 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Barrett, Anthony G. M. published the artcileSynthetic studies on calyculin A: a convenient asymmetric synthesis of anti-vicinal diols, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1994), 1901-5, database is CAplus.

Anti-vicinal diols, e.g. I [R = Ph, cyclohexyl, (CH₂)₅Me] and II, have been prepared with excellent relative and absolute stereocontrol via the reaction of aldehydes with B-{3-[(diisopropylamino)dimethylsilyl]allyl}diisopinocampheylborane in THF and Et₂O and work-up using potassium fluoride, potassium hydrogen carbonate and hydrogen peroxide in aqueous methanol. Absolute stereoselectivities of reactions were determined by conversion of four product diols into bis[(R)-α-methoxy-α-(trifluoromethyl)phenylacetate] esters. The reactions are relevant to the synthesis of the marine phosphatase inhibitor calyculin A.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Barrett, Anthony G. M. published the artcileB-[3-((Diisopropylamino)dimethylsilyl)allyl]diisopinocampheylborane: an excellent reagent for the stereoselective synthesis of anti vicinal diols, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane, the publication is Journal of Organic Chemistry (1991), 56(18), 5243-5, database is CAplus.

Title reagent I, derived from (+)-α-pinene, reacted with aldehydes to provide, on work up with hydrogen peroxide, (3S,4R)-dihydroxy-1-alkenes. These were formed with both high relative and absolute stereochem. control. The antipodal reagent, derived from (-)-α-pinene, gave the corresponding (3R,4S)-diols.

Journal of Organic Chemistry published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem