Category: 99438-28-5

Wipf, Peter published the artcileSynthesis and Biological Evaluation of Structurally Highly Modified Analogues of the Antimitotic Natural Product Curacin A, Computed Properties of 99438-28-5, the publication is Journal of Medicinal Chemistry (2002), 45(9), 1901-1917, database is CAplus and MEDLINE.

Structure-activity relationship anal. of synthetic analogs of curacin A revealed the lack of activity of traditional heterocyclic replacements of the thiazoline ring or cyclopropyl analogs of the core diene segment. The significance of the C(3)-C(4)-(Z)-alkene geometry was established, and a novel oxime analog was designed that displays biol. properties that are a close match of the natural product lead. The much less lipophilic, structurally simplified oxime I was only slightly weaker at inhibiting the growth of cultured human tumor cells than the natural product and was found to be more potent than curacin A at inhibiting the assembly of purified tubulin. Accordingly, the oxime moiety is likely to serve as a novel bioisostere of the (Z)-alkene group.

Journal of Medicinal 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 C3H6O2, Computed Properties of 99438-28-5.

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

Gao, Xuguang published the artcileTotal synthesis of the putative structure of the proposed Banyasin A, COA of Formula: C21H37BO, the publication is Frontiers in Chemistry (Lausanne, Switzerland) (2015), 1-7, database is CAplus and MEDLINE.

The first total synthesis of four possible isomers of a mol. possessing the configuration proposed for Banyasin A is described. The structure synthesized appears to be different from that of the natural product.

Frontiers in Chemistry (Lausanne, Switzerland) 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, COA of Formula: C21H37BO.

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

Huh, Chan Woo published the artcileHighly Stereoselective and Modular Syntheses of 10-Hydroxytrilobacin and Three Diastereomers via Stereodivergent [3 + 2]-Annulation Reactions, Category: ethers-buliding-blocks, the publication is Organic Letters (2008), 10(15), 3371-3374, database is CAplus and MEDLINE.

A convergent synthesis of the annonaceous acetogenin, 10-hydroxytrilobacin (I), was accomplished by using the [3+2]-annulation reaction of tetrahydrofuranyl carboxaldehyde II and allylsilane III. The stereodivergency of the [3+2]-annulation reaction made it possible to achieve modular, highly stereoselective syntheses of three 10-hydroxytrilobacin diastereomers from the same precursors by using simple modifications of reaction conditions.

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, Category: ethers-buliding-blocks.

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

Sun, Huikai published the artcileSynthesis of (+)-B-allyldiisopinocampheylborane and its reaction with aldehydes, Application In Synthesis of 99438-28-5, the publication is Organic Syntheses (2011), 87-101, database is CAplus and MEDLINE.

(+)-B-allyldiisopinocampheylborane (I) was prepared from (+)-B-methoxydiisopinocampheylborane and allylmagnesium bromide. Allylboration of achiral aldehydes by I gave secondary homoallylic alcs. stereoselectively. E.g., reaction of I and MeCHO gave 74% alc. (II). Allylboration of chiral aldehydes was also studied.

Organic Syntheses 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 C28H41N2P, Application In Synthesis of 99438-28-5.

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

Paterson, Ian published the artcileSynthetic studies towards iriomoteolide 1a: stereocontrolled construction of C1-C9 and C11-C23 segments using lactate aldol chemistry, HPLC of Formula: 99438-28-5, the publication is Synlett (2010), 571-574, database is CAplus.

Nonracemic undecenal I (TES = Et₃Si) and nonracemic butenyldihydropyranone II (PMB = 4-MeOC₆H₄CH₂), C13-C23 and C1-C9 segments of the cytotoxic macrolide iriomoteolide 1a III, are prepared using stereoselective boron-mediated aldol additions (using both enantiomers of a nonracemic lactate-derived ketone) and a Suzuki-Miyaura cross-coupling reaction as the key steps.

Synlett 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, HPLC of Formula: 99438-28-5.

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

Brown, Herbert C. published the artcileB-2′-Isoprenyldiisopinocampheylborane: an efficient reagent for the chiral isoprenylation of aldehydes. A convenient route to both enantiomers of ipsenol and ipsdienol, Related Products of ethers-buliding-blocks, the publication is Tetrahedron Letters (1990), 31(4), 455-8, database is CAplus.

B-2′-Isoprenyldiisopinocampheylborane is prepared by metalation of isoprene with potassium 2,2,5,5-tetramethylpiperidide followed by sequential treatment with B-methoxydiisopinocampheylborane and boron trifluoride-etherate. Condensation of this reagent with aldehydes provides isoprenylated chiral alcs. This methodol. is utilized for an efficient one-pot synthesis of both enantiomers of the pheromones of the bark beetle Ips paraconfusus Lanier, ipsenol (I) and ipsdienol (II) in 96% ee and 65% isolated yield.

Tetrahedron 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, Related Products of ethers-buliding-blocks.

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

Brown, Gerbert C. published the artcileChiral synthesis via organoboranes. 26. An efficient synthesis of isoprenyl derivatives of borane. Valuable reagents for the isoprenylboration of aldehyde. A convenient route to both enantiomers of ipsenol and ipsdienol in high optical purity, COA of Formula: C21H37BO, the publication is Tetrahedron (1990), 46(13-14), 4463-72, database is CAplus.

Preparation of B-isoprenyldialkylboranes is achieved by adopting the Brandsma modification of the Schlosser procedure, namely metalation of isoprene with potassium 2,2,5,5-tetramethylpiperidide followed by sequential treatment with B-methoxydialkylborane and boron trifluoride-etherate. These reagents are used for the convenient isoprenylation of aldehydes. Reaction of isovaleraldehyde and β,β-dimethylacrolein with B-2′-isoprenyldiisopinocampheylborane (I) provides both ipsenol (II) and ipsdienol (III), resp. in 65% yields and 96% ee.

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, COA of Formula: C21H37BO.

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

Lu, Hai-Hua published the artcileSynthesis and Biological Evaluation of Paleo-Soraphens, Application In Synthesis of 99438-28-5, the publication is Angewandte Chemie, International Edition (2013), 52(51), 13549-13552, database is CAplus and MEDLINE.

Possible natural product precursors of soraphen A [(1R,2S,5S,10S,11R,12E,14S,15S,16S,17S,18R)-1,17-dihydroxy-10,11,18-trimethoxy-2,14,16-trimethyl-5-phenyl-4,19-dioxabicyclo[13.3.1]nonadec-12-en-3-one] (I) were prepared The synthesis of the target compounds was achieved by a multistep process. The title compounds thus formed included a precursor for soraphen A (II) and a precursor for soraphen B (III). The title compounds were evaluated against Pythium debaryanum, Mucor hiemalis, Botrytis cinerea (fungal pathogens, antifungal agents) and against animal cell line L-929 (mouse connective tissue fibroblast cell line), animal cell line KB-3-1, human cervical carcinoma cell line (anticancer agents, antitumor agents). The compounds were evaluated as deoxyribonucleate topoisomerase I inhibitors.

Angewandte Chemie, International Edition 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, Application In Synthesis of 99438-28-5.

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

Brown, Herbert C. published the artcileChiral synthesis via organoboranes. 9. Crystalline chelates from borinic and boronic esters. A simple procedure for upgrading borinates and boronates to materials approaching 100% optical purity, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane, the publication is Journal of Organic Chemistry (1986), 51(24), 4526-30, database is CAplus.

The synthesis of crystalline chelates from borinate and boronate esters was explored as a means of upgrading the optical purities of intermediates from asym. hydroboration. B-Methoxy-9-borabicyclo[3.3.1]nonane and Me dicyclohexyl- and diisopinocampheylborinate react with various amino alcs. to form the corresponding chelates. Crystallization of 2-pyrrolidinylmethyl isopinocampheyl exo-norbornylborinate of 83% enantiomeric excess (e.e.) gives a product approaching 100% e.e. Treating di-Me cyclopentyl-, exo-norbornyl- and siamylboronate with various amino diols gave the corresponding boronates. The formation of the B←N bond depends on both steric and electronic factors. The corresponding boronates (2:1 derivatives) derived from these typical di-Me boronates and tetrols were also prepared The chelate derived from di-Et 3-tetrahydropyranylboronate of 83% e.e. and (HOCH₂CH₂)₂NCH₂CH₂N(CH₂CH₂OH)₂ yields a product of optical purity ≤100% e.e. upon crystallization

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

Ramachandran, P. Veeraraghavan published the artcilePreparative-scale synthesis of both antipodes of B-γ,γ-dimethylallyldiisopinocampheylborane: application for the synthesis of C₁-C₆ subunit of epothilone, HPLC of Formula: 99438-28-5, the publication is Tetrahedron Letters (2004), 45(5), 1011-1013, database is CAplus.

A preparative-scale synthesis of B-γ,γ-dimethylallyldiisopinocampheylborane starting from prenyl alc. has been described. This reagent, upon reaction with various aldehydes, provides the corresponding α,α-dimethylhomoallylic alcs. in high enantioselectivities. The application of this reagent has been demonstrated for the synthesis of C₁-C₆ subunit of epothilone.

Tetrahedron 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, HPLC of Formula: 99438-28-5.

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