Category: 99438-28-5

Della Sala, Giorgio published the artcileTowards the biosynthesis of the aromatic products of the Mediterranean mollusc Scaphander lignarius: isolation and synthesis of analogues of lignarenones, Category: ethers-buliding-blocks, the publication is Tetrahedron (2007), 63(30), 7256-7263, database is CAplus.

Secondary metabolites of the Mediterranean mollusc Scaphander lignarius from different collection sites have been investigated, proving the constant presence of a number of minor metabolites correlated to the already known lignarenones. Complete characterization of the new metabolites has been supported by enantioselective synthesis. The data are consistent with the origin of this unique class of ω-phenyloctanoids from a common polyketide pathway.

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, Category: ethers-buliding-blocks.

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

Smith, Amos B. III published the artcileTotal Synthesis of (-)-2-epi-Peloruside A, Synthetic Route of 99438-28-5, the publication is Organic Letters (2008), 10(24), 5501-5504, database is CAplus and MEDLINE.

A convergent synthesis of (-)-2-epi-peloruside A has been achieved. Highlights include implementation of multi-component type I anion relay chem. (ARC) to unite 2-TBS-1,3-dithiane with two epoxides to construct the eastern hemisphere, a late-stage dithiane union to secure the complete, fully functionalized carbon backbone, and Yamaguchi macrolactonization, which led to (-)-2-epi-peloruside A via an unexpected epimerization at C(2).

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 C5H10O, Synthetic Route of 99438-28-5.

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

Li, Yingfa published the artcileA formal synthesis of ionomycin featuring a permanganate-mediated oxidative cyclisation, Quality Control of 99438-28-5, the publication is Synthesis (2011), 104-108, database is CAplus.

Key steps in a synthesis of the C17-C32 fragment (I) of ionomycin are (a) an auxiliary-directed oxidative cyclization of a diene with potassium permanganate to construct a THF ring and four stereogenic centers in a single operation, and (b) a chain-appendage reaction featuring the alkylation of an enolsilane by an oxocarbenium ion generated from a 2-phenylsulfonyl-substituted THF.

Synthesis 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, Quality Control of 99438-28-5.

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

Kim, Hak Joong published the artcileChemoenzymic Synthesis of Spinosyn A, COA of Formula: C21H37BO, the publication is Angewandte Chemie, International Edition (2014), 53(49), 13553-13557, database is CAplus and MEDLINE.

Following the biosynthesis of polyketide backbones by polyketide synthases (PKSs), post-PKS modifications result in a significantly elevated level of structural complexity that renders the chem. synthesis of these natural products challenging. We report herein a total synthesis of the widely used polyketide insecticide spinosyn A by exploiting the prowess of both chem. and enzymic methods. As more polyketide biosynthetic pathways are characterized, this chemoenzymic approach is expected to become readily adaptable to streamlining the synthesis of other complex polyketides with more elaborate post-PKS modifications.

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, COA of Formula: C21H37BO.

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

Ramachandran, P. Veeraraghavan published the artcileStudies towards the synthesis of epothilone A via organoboranes, Formula: C21H37BO, the publication is Organic & Biomolecular Chemistry (2005), 3(20), 3812-3824, database is CAplus and MEDLINE.

Studies towards the synthesis of epothilone A via organoboranes have been described. A modified procedure for the large-scale preparation of B-γ,γ-dimethylallyldiisopinocampheylborane from prenyl alc. has been developed. This reagent, upon reaction with various aldehydes RCHO (R = Et, Ph, 4-MeOC₆H₄CH₂OCH₂CH₂, etc.), provides the corresponding α,α-dimethylhomoallylic alcs. I in high enantioselectivities. The application of this reagent for the synthesis of the C₁-C₆ subunit II of epothilone has been demonstrated. Alternatively, inter- and intramol. asym. reduction protocols have also been utilized for the synthesis of the C₁-C₆ subunit of epothilone A. The synthesis of the C₇-C₂₁ fragment III of epothilone A involving asym. alkoxyallyl- and crotylboration using α-pinene-derived reagents has also been described.

Organic & Biomolecular 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

Barry, Conor S. published the artcileStereoselective Synthesis of the Tetrahydropyran Core of Polycavernoside A, SDS of cas: 99438-28-5, the publication is Organic Letters (2005), 7(13), 2683-2686, database is CAplus and MEDLINE.

A concise and stereoselective synthesis of the tetra-substituted tetrahydropyran core of polycavernoside A was achieved in 55% overall yield from 3-benzyloxypropanal. A stereoselective allyl transfer reaction was used in the synthesis of enol ether I followed by a TFA-mediated cyclization to create the three new asym. centers in the tetrahydropyran with complete stereocontrol in a single-pot process.

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

Hertweck, Christian published the artcileAsymmetric α-Chloroallylboration of Amino Aldehydes: A Novel and Highly Versatile Route to D– and L-erythro-Sphingoid Bases, Name: (+)-B-Methoxydiisopinocampheylborane, the publication is Journal of Organic Chemistry (1999), 64(12), 4426-4430, database is CAplus.

Serinal-derived vinyloxiranes represent versatile building blocks for synthesis of D-(or L-)erythro-sphingosine and its analogs. Asym. α-chloroallylation of the Garner aldehyde with chiral and achiral γ-(Z)-chloroallylboranes, followed by DBU-mediated cyclization of the corresponding chlorohydrins, provides a highly effective route to oxazolidine vinyloxiranes in high yield under mild conditions. Matched and mismatched cases of the double diastereoselective allylation were investigated. The vinyloxirane reacts with a variety of organocuprates by a S_N2′ type nucleophilic substitution, yielding protected sphingoid bases as (E)-allylic alcs. exclusively. By the new approach, a multitude of different sphingoid core structures becomes available, from a uniform protocol, with high yield and efficiency.

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, Name: (+)-B-Methoxydiisopinocampheylborane.

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

Hertweck, Christian published the artcileTandem Reduction-Chloroallylboration of Esters: Asymmetric Synthesis of Lamoxirene, the Spermatozoid Releasing and Attracting Pheromone of the Laminariales (Phaeophyceae), Product Details of C21H37BO, the publication is Journal of Organic Chemistry (2000), 65(8), 2458-2463, database is CAplus and MEDLINE.

Asym. synthesis of all four stereoisomers of lamoxirene (cis-2-cyclohepta-2,5-diene-3-vinyloxirane), the spermatozoid-releasing and -attracting pheromone of the Laminariales (Phaeophyceae), is reported. Chiral Et cyclohepta-2,5-diene carboxylates, prepared by a divinylcyclopropane Cope rearrangement, were effectively alkylated by means of a novel tandem DIBAL-H reduction/asym. α-chloroallylboration using (Z)-γ-chloroallyldiisopinocampheylboranes. The ensuing syn-α-chlorohydrins were transformed into the corresponding vinyloxiranes with DBU, providing all four isomers of the pheromone in good chem. and excellent optical yield (90-97% ee). Spermatozoid-release assays were conducted with the sympatrically growing species L. digitata, L. hyperborea, and L. saccharina and established I as the most active isomer in all cases.

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, Product Details of C21H37BO.

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

Hertweck, Christian published the artcileB-methoxydiisopinocampheylborane (Ipc₂BOMe). A pinene-based auxiliary for asymmetric C-C bond-forming reactions, Quality Control of 99438-28-5, the publication is Journal fuer Praktische Chemie (Weinheim, Germany) (1999), 341(1), 83-87, database is CAplus.

A review with 31 references B-methoxydiisopinocampheylborane is a highly versatile chiral auxiliary that is compatible with a great variety of functional groups, either in the reagent or the substrate. Thus, this reagent allows direct access to complex mols. without extensive use of protecting groups. Of particular advantage is the ability of heteroatom substituents on the B reagents, to affect the stereochem. course of the reaction. This can then be used to yield products of predictable and well defined relative and absolute stereochem.

Journal fuer Praktische Chemie (Weinheim, Germany) 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, Quality Control of 99438-28-5.

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

Nicolaou, K. C. published the artcileSynthesis of iso-epoxy-amphidinolide N and des-epoxy-caribenolide I structures. Initial forays, Quality Control of 99438-28-5, the publication is Organic & Biomolecular Chemistry (2006), 4(11), 2119-2157, database is CAplus and MEDLINE.

Two strategies for the projected total synthesis of the phenomenally potent antitumor macrolides amphidinolide N and caribenolide I are described. The title compounds are introduced as challenging and unique targets for chem. synthesis, and their retrosynthetic anal. is presented. The synthesis of the four defined key building blocks, required for the construction of amphidinolide N, in their enantiomerically pure forms, is described, followed by the coupling through hydrazone alkylation processes to generate the complete C6-C29 carbon framework (I) of the target compound Fusion of the remaining C1-C5 sector onto the mol. by metathesis-based methods was unsuccessful, resulting in the adoption of a second-generation strategy which called for the employment of one of the array of palladium-catalyzed cross-coupling reactions to generate the C5-C6 carbon-carbon bond. Vinyl bromide II, representing the C6-C29 skeleton of caribenolide I, was prepared through the sequential alkylation, but failed to engage in the appropriate cross-coupling reaction with a variety of C1-C4 partners. Despite these setbacks, the information gleaned from these endeavors was to prove invaluable in laying the foundation for the eventual successful approach to the macrocyclic structures of amphidinolide N and caribenolide I.

Organic & Biomolecular 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, Quality Control of 99438-28-5.

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