Category: 99438-28-5

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

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

Yadav, J. S. published the artcileStereoselective total synthesis of (+)-sapinofuranone B, Related Products of ethers-buliding-blocks, the publication is Tetrahedron (2011), 67(25), 4620-4627, database is CAplus.

Two approaches for the total synthesis of (+)-sapinofuranone B have been described. The first strategy utilizes the methodol. developed earlier in our group to get the chiral propargyl alc. and the second strategy involves generation of threo-1,2-diol derivative by diastereoselective and enantioselective addition of [(Z)-γ-methoxymethoxyallyl]diisopinocampheylborane onto aldehyde and cross metathesis as the key steps.

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 C6H4ClNO2, Related Products of ethers-buliding-blocks.

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

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

Gui, Honggang published the artcileCross-metathesis approach for stereocontrolled synthesis of the C1-C15 fragment of rhizopodin, COA of Formula: C21H37BO, the publication is Synlett (2014), 25(1), 138-142, database is CAplus.

The C1-C15 fragment of rhizopodin was synthesized through either Suzuki coupling reaction of vinyl iodide and vinyl boronate or cross-metathesis of a terminal olefin and a diene adduct in the presence of Hoveyda-Grubbs II catalyst.

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, COA of Formula: C21H37BO.

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

Zhang, Wei published the artcileResearch progress of apratoxin A: a marine cyclic-depsipeptide with significant anticancer activity, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane, the publication is Youji Huaxue (2014), 34(3), 475-484, database is CAplus.

Apratoxin A, a marine natural cyclic-depsipeptide bearing novel and complex structure, showed significant antiproliferative activity against several cancer cell lines. A brief introduction on the research progress of this natural product including total synthesis, structure-activity relationship, pharmacol. studies, and biosynthetic pathway was summarized.

Youji Huaxue 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 C10H12O5, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane.

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

Mukherjee, Sumit published the artcileApplication of Tandem Ring-Closing Enyne Metathesis: Formal Total Synthesis of (-)-Cochleamycin A, Application of (+)-B-Methoxydiisopinocampheylborane, the publication is Organic Letters (2009), 11(13), 2916-2919, database is CAplus and MEDLINE.

A tandem ring-closing metathesis of a silaketal-based dienyne substrate proceeded efficiently to provide a bicyclic siloxane, which upon removal of the silicon tether afforded an (E,Z)-1,3-dienediol. Further manipulation of this key functional motif rendered synthesis of the entire C1-C19 linear skeleton of (-)-cochleamycin A (I) , a late-stage intermediate employed in the previous total synthesis of (+)-cochleamycin A by Roush and co-workers.

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, Application of (+)-B-Methoxydiisopinocampheylborane.

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

Stockdale, Tegan P. published the artcileA synthesis-enabled relative configurational assignment of the C31-C46 region of hemicalide, HPLC of Formula: 99438-28-5, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(38), 5729-5732, database is CAplus and MEDLINE.

Herein, through the targeted synthesis of configurationally defined fragments, as well as “encoded” mixtures of diastereomers, the stereochem. elucidation of the C31-C46 region of hemicalide I was achieved. Detailed NMR spectroscopic anal. of candidate fragments and comparison with the related hemicalide data strongly supported a 31,32-syn, 32,36-anti and 42,46-anti relationship. In combination with previous work on hemicalide, this reduced the number of possible structural permutations down to a more manageable eight diastereomers.

Chemical Communications (Cambridge, United Kingdom) 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 C15H12O6, HPLC of Formula: 99438-28-5.

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

White, James D. published the artcileTotal Synthesis of Phorboxazole A. 1. Preparation of Four Subunits, Category: ethers-buliding-blocks, the publication is Organic Letters (2006), 8(26), 6039-6042, database is CAplus and MEDLINE.

Four subunits (I–IV) of the potent antitumor agent phorboxazole A were constructed. Fragments C20-C32 (I) and C9-C19 (II) containing tetrahydropyrans A and B, resp., were assembled using palladium-catalyzed intramol. alkoxycarbonylation.

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 C14H18BClO4, Category: ethers-buliding-blocks.

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