Category: 99438-28-5

Hu, Shaojing published the artcileDiastereo- and Enantioselective Synthesis of syn-α-Vinylchlorohydrins and cis-Vinylepoxides, Formula: C21H37BO, the publication is Journal of Organic Chemistry (1996), 61(21), 7513-7520, database is CAplus and MEDLINE.

A new method to generate chiral syn-vinylchlorohydrins and cis-vinyloxiranes is reported. Reaction of (α-haloallyl)lithiums with methoxy-9-BBN or Ipc₂BOMe followed by treatment with BF₃·OEt₂ leads to (Z)-(γ-haloallyl)boranes which react with aldehydes to yield cis-vinylepoxides (de ≥ 90%) upon oxidative workup. Alternatively, addition of ethanolamine to the allylboration product yields syn-α-halohydrins (de ≥ 90%) that are also easily cyclized to cis-vinylepoxides. Extension of this protocol using [(Z)-γ-chloroallyl]BIpc₂ leads to chiral syn-α-chlorohydrins and cis-vinylepoxides in high de (≥90%) and ee (90-99%). Enantioselectivity of reactions of chiral (Z)-(γ-chloroallyl)boranes with aldehydes are more sensitive to reaction conditions than enantioselectivity of reactions of other α- or γ-substituted allylboranes. The effects of proportion of BF₃·OEt₂ and the relative efficacies of LiNR₂ bases on diastereo- and enantioselectivity of the chloroallylation are reported.

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

Brown, Herbert C. published the artcileChiral synthesis via organoboranes. 13. A highly diastereoselective and enantioselective addition of [(Z)-γ-alkoxyallyl]diisopinocampheylboranes to aldehydes, COA of Formula: C21H37BO, the publication is Journal of the American Chemical Society (1988), 110(5), 1535-8, database is CAplus.

Isomerically pure [(Z)-γ-methoxyallyl]diisopinocampheylboranes, I, prepared from (+)-α-pinene and II, have been prepared from B-methoxydiisopinocampheylborane and lithiated allyl Me ether. These enantiomeric [(Z)-γ-methoxyallyl]diisopinocampheylboranes retain their stereochem. identity under the reaction conditions. They have been successfully condensed with various aldehydes, such as acetaldehyde, propionaldehyde, 2-methylpropionaldehyde, and benzaldehyde in a regioselective and stereoselective manner to yield the corresponding threo-β-methoxyhomoallyl alcs. in â‰?9% diastereoselectivities and â‰?5% enantioselectivities. Similarly, [(Z)-γ-[(methoxymethyl)oxy]allyl]diisopinocampheylborane was prepared and was utilized for the preparation of threo-1,2-diol.

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 C21H37BO, COA of Formula: C21H37BO.

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

Mizukami, Daichi published the artcileTandem Macrolactone Synthesis: Total Synthesis of (-)-Exiguolide by a Macrocyclization/Transannular Pyran Cyclization Strategy, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane, the publication is Angewandte Chemie, International Edition (2022), 61(22), e202202549, database is CAplus and MEDLINE.

Tetrahydropyran-containing macrolactones were synthesized by integrating Meyer-Schuster rearrangement, macrocyclic ring-closing metathesis, and transannular oxa-Michael addition under gold and ruthenium catalysis. Single-step access to a variety of 14- to 20-membered macrolactones containing a tetrahydropyran ring was possible from readily available linear precursors in good yields and with moderate to excellent diastereoselectivity. A 13-step synthesis of (-)-exiguolide (I), an anticancer marine macrolide, showcased the feasibility of our tandem reaction sequence for macrolactone synthesis and also demonstrated the power of transannular reactions for rapid assembly of the tetrahydropyran rings of the target natural product.

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, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane.

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

White, James D. published the artcileA concise synthesis of the cytotoxic depsipeptide arenastatin A, Name: (+)-B-Methoxydiisopinocampheylborane, the publication is Tetrahedron Letters (1998), 39(48), 8779-8782, database is CAplus.

Arenastatin A (I) (cryptophycin 24) was synthesized by convergence of hydroxy ester II with amino acid derivative III. Two independent and highly efficient routes to II are disclosed.

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 C4Br2N2O4S, Name: (+)-B-Methoxydiisopinocampheylborane.

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

Brown, Herbert C. published the artcileChiral synthesis via organoboranes. XVI. Boroxazolidones derived from α-amino acids and borinic or boronic esters. A simple procedure for upgrading borinates and boronates to materials of high optical purity, Category: ethers-buliding-blocks, the publication is Journal of Organometallic Chemistry (1988), 341(1-3), 73-81, database is CAplus.

The synthesis of boron heterocycles from borinic and boronic esters with α-amino acids was explored as a means of upgrading the optical purities of intermediates from asym. hydroboration. B-Methoxy-9-borabicyclo[3.3.1]nonane, Me dicyclohexylborinate, and (+)- and (-)-Me diisopinocampheylborinate react with various α-amino acids to form the corresponding crystalline chelates. Recrystallization of the chelates derived from Me trans-2-phenylcyclopentylisopinocampheylborinate of 85% enantiomeric excess (ee) with L-phenylalanine, Me isopinocampheyl-exo-norbornylborinate of 83% ee with L-proline, and both optical isomers of Me diisopinocampheylborinate of 92% ee with L-proline yield the corresponding products with optical purities approaching 100% ee. Di-Me cyclopentylboronate, di-Me exo-norbornylboronate, and di-Me isopinocampheylboronate upon treatment with iminodiacetic acid and N-methyliminodiacetic acid form the corresponding bicyclic boronates. Recrystallization of the chelate derived from di-Et 3-tetrahydropyranylboronate and iminodiacetic acid yields a product of essentially 100% ee. Consequently, formation of boroxazolidones of asym. hydroboration products provides one possible route to upgrade such products to materials of high optical purity.

Journal of Organometallic 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, Category: ethers-buliding-blocks.

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

Li, Fangzheng published the artcileEfficient Stereoselective Synthesis of a Key Chiral Aldehyde Intermediate in the Synthesis of Picolinamide Fungicides, Formula: C21H37BO, the publication is Organic Process Research & Development (2019), 23(10), 2253-2260, database is CAplus.

A highly stereoselective and efficient synthesis of (4S,5S,6S)-6-(benzyloxy)-5-phenoxy-4-propoxyheptanal, a key intermediate for syntheses of picolinamide fungicides, is described in this report. The synthesis features a scalable allylpropyl ether preparation, an efficient synthesis of the C1-C3 anti,syn-(S,S,S) stereotriad via a highly diastereoselective allylboration, and Cu-catalyzed phenylation of a sterically hindered secondary alc. with BiPh₃(OAc)₂ followed by highly regioselective hydroformylation with the formation of a linear aldehyde. Excellent overall route efficiency was achieved (six steps and 39% yield) starting from readily available and inexpensive (S)-Et lactate.

Organic Process Research & Development 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

Reddy, Y. Krishna published the artcileAsymmetric Total Synthesis of (+)-Fostriecin, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane, the publication is Organic Letters (2002), 4(6), 969-971, database is CAplus and MEDLINE.

(+)-Fostriecin (I), a potent protein phosphatase inhibitor and anticancer agent, was prepared by an efficient, multi-convergent asym. synthesis. Key transformations include a ring forming olefin metathesis leading to the α,β-unsaturated lactone II and creation of the triene moiety via Suzuki cross-coupling.

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, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane.

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

Hassfeld, Jorma published the artcileSynthesis of the C1-C17 macrolactone of tedanolide, Related Products of ethers-buliding-blocks, the publication is Synthesis (2005), 1183-1199, database is CAplus.

The vinylogous Mukaiyama aldol reaction is a useful method to build up complex polyketide structures. It is successfully employed in the synthesis of the C1-C17 macrolactone of tedanolide, a highly cytotoxic marine natural product. These studies present a practical approach toward the total synthesis of tedanolide; it is pursued using the appropriate C13-C23 segment that is introduced by a pivotal aldol reaction to join both hemispheres.

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, Related Products of ethers-buliding-blocks.

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

Tsuruda, Takeshi published the artcileStereoselective Synthesis of the C1-C29 Part of Amphidinol 3, Quality Control of 99438-28-5, the publication is Journal of Organic Chemistry (2015), 80(2), 859-871, database is CAplus and MEDLINE.

Stereoselective synthesis of the C1-C29 part (I) of amphidinol 3 (AM3) was achieved. The C1-C20 part was assembled from three building blocks via regioselective cross metathesis to form the C4-C5 double bond and addition of an alkenyllithium and a lithium acetylide to two Weinreb amides followed by asym. reduction to form the C9-C10 and C14-C15 bonds, resp. The C21-C29 part was synthesized via successive cross metathesis and oxa-Michael addition sequence to construct the 1,3-diol system at C25 and C27 and Brown asym. crotylation to introduce the stereogenic centers at C23 and C24. Coupling of the C1-C20 and C21-C29 parts was achieved by Julia-Kocienski olefination and regio- and stereoselective dihydroxylation of the C20-C21 double bond in the presence of the C4-C5 and C8-C9 double bonds to afford the C1-C29 part of AM3.

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 C3H5BN2O2, Quality Control of 99438-28-5.

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

Zampella, Angela published the artcileStereoselective synthesis of (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid and determination of the absolute stereochemistry of the natural product from callipeltin A, Quality Control of 99438-28-5, the publication is Tetrahedron: Asymmetry (2002), 13(12), 1237-1239, database is CAplus.

A revised stereostructure of 3-hydroxy-2,4,6-trimethylheptanoic acid, the β-hydroxy acid that acylates the N-terminus of callipeltin A, is proposed on the basis of anal. of J-coupling in the ¹H NMR spectrum of the acetonide derivative obtained from the acid hydrolyzate of callipeltin A. The proposed structure was definitively confirmed by enantioselective synthesis.

Tetrahedron: Asymmetry 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 C7H13NO2, Quality Control of 99438-28-5.

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