Category: 99438-28-5

Karisalmi, Kaisa published the artcileStereoselective synthesis of the C₉-C₁₉ lactone-dipropionate fragment of calyculin C, Computed Properties of 99438-28-5, the publication is Tetrahedron Letters (2004), 45(44), 8245-8248, database is CAplus.

A highly diastereoselective synthesis of the title fragment (I) of calyculin C has been developed based on an internal asym. induction between a chiral aldehyde and Z-crotyl trifluorosilane.

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, Computed Properties of 99438-28-5.

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

Habrant, Damien published the artcileTowards the total synthesis of calyculin C: preparation of the C₉-C₂₅ spiroketal-dipropionate unit, Computed Properties of 99438-28-5, the publication is Organic & Biomolecular Chemistry (2010), 8(19), 4364-4373, database is CAplus and MEDLINE.

An asym. synthesis of the C₉-C₂₅ spiroketal fragment of calyculin C is described. Key steps include two crotylation reactions using successively Brown’s reagent and (Z)-crotyltrifluorosilane for the formation of the anti, anti, anti stereo-tetrad, ynone formation by a Pd-catalyzed coupling of a thiol ester with a terminal alkyne and a double intramol. hetero-Michael addition for the stereoselective construction of the spiroketal framework.

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, Computed Properties of 99438-28-5.

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

Tan, Choon-Hong published the artcileStereochemical assignment of the C21-C38 portion of the desertomycin/oasomycin class of natural products by using universal NMR databases: Proof, Quality Control of 99438-28-5, the publication is Angewandte Chemie, International Edition (2000), 39(23), 4282-4284, database is CAplus and MEDLINE.

We have predicted the stereochem. of the C21-C38 portion of the desertomycin/oasomycin class of natural products and have proven the predicted stereochem. by a stereoselective synthesis of the C21-C38 degradation 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 C5H4N4, Quality Control of 99438-28-5.

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

Denmark, Scott E. published the artcileTotal synthesis of (+)-papulacandin D, Name: (+)-B-Methoxydiisopinocampheylborane, the publication is Tetrahedron (2010), 66(26), 4745-4759, database is CAplus and MEDLINE.

A total synthesis of (+)-papulacandin D (I) was achieved in 31 steps, in a 9.2% overall yield from com. available materials. The synthetic strategy divided the mol. into two nearly equal sized subunits, i.e. the spirocyclic C-arylglycopyranoside and the polyunsaturated fatty acid side-chain. The C-arylglycopyranoside was prepared in 11 steps in a 30% overall yield from triacetoxyglucal. The fatty acid side-chain was also prepared in 11 steps in a 30% overall yield from geraniol. The key strategic transformations in the synthesis were a palladium-catalyzed organosilanolate-based cross-coupling reaction of a dimethylglucal-silanol with an electron-rich and sterically hindered aromatic iodide and a Lewis-base catalyzed enantioselective allylation reaction of a dienal and allyltrichlorosilane. A critical element in the successful execution of the synthesis was the development of a suitable protecting group strategy that satisfied a number of stringent criteria.

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

Wang, Pengfei published the artcileSynthesis of the Potent Immunostimulatory Adjuvant QS-21A, Formula: C21H37BO, the publication is Journal of the American Chemical Society (2005), 127(10), 3256-3257, database is CAplus and MEDLINE.

QS-21A is one of the most promising new adjuvants for immune response potentiation and dose-sparing in vaccine therapy, given its exceedingly high level of potency and its favorable toxicity profile. Melanoma, breast cancer, small cell lung cancer, prostate cancer, HIV-1, and malaria are among the numerous maladies targeted in more than 80 recent and ongoing clin. trials involving QS-21A as a critical component for immune response augmentation in microgram doses. Herein is reported the first synthesis and structure verification of QS-21A_api, applying novel glycosylation methodologies in the convergent modular construction of this rare and potent natural product immunostimulant (no biol. data).

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 C15H21BO3, Formula: C21H37BO.

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

Son, Jung Beom published the artcileEnantioselective total synthesis of (-)-clavosolide A and B, Category: ethers-buliding-blocks, the publication is Bulletin of the Korean Chemical Society (2010), 31(3), 653-663, database is CAplus.

Enantioselective total synthesis of proposed and revised structure of (-)-clavosolide A and B by a convergent approach, where syn-selective aldol, hydroxy-directed cyclopropanation, Mitsunobu inversion, Schmidt-type glycosylation, and macrolactonization reactions were utilized as key reactions. The relative and absolute stereochem. of the natural products were confirmed unambiguously by comparing the optical rotation values and ¹H and ¹³C NMR spectra of them.

Bulletin of the Korean 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 C9H5ClO2, Category: ethers-buliding-blocks.

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

Hattori, Hiromu published the artcileTotal Synthesis of Tiacumicin A. Total Synthesis, Relay Synthesis, and Degradation Studies of Fidaxomicin (Tiacumicin B, Lipiarmycin A3), Related Products of ethers-buliding-blocks, the publication is Journal of Organic Chemistry (2018), 83(13), 7180-7205, database is CAplus and MEDLINE.

The com. macrolide antibiotic fidaxomicin was synthesized in a highly convergent manner. Salient features of this synthesis include a β-selective noviosylation, a β-selective rhamnosylation, a ring closing metathesis, a Suzuki coupling and a vinylogous Mukaiyama aldol reaction. Careful choice of protecting groups and fine tuning of the glycosylation reactions led to the first total synthesis of fidaxomicin. In addition, a relay synthesis of fidaxomicin was established, which gives access to a conveniently protected intermediate from the natural material for derivatization. The first total synthesis of a related congener, tiacumicin A, is presented.

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, Related Products of ethers-buliding-blocks.

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

Nicolaou, K. C. published the artcileTotal Synthesis and Biological Evaluation of Monorhizopodin and 16-epi-Monorhizopodin, Safety of (+)-B-Methoxydiisopinocampheylborane, the publication is Angewandte Chemie, International Edition (2011), 50(5), 1139-1144, S1139/1-S1139/94, database is CAplus and MEDLINE.

A highly convergent total synthesis of monorhizopodin (I) and 16-epi-monorhizopodin was developed, rendering the monomeric homologs of the powerful antitumor agent rhizopodin available for biol. investigations. Preliminary studies showed these compounds to be endowed with actin-binding properties but devoid of any associated cytotoxicity, thus posing interesting questions regarding the role of the dimeric nature of rhizopodin in its mode of action. Further studies directed toward the elucidation of the mechanism of action and the differences of rhizopodin and its monomeric homologs, monorhizopodin and 16-epi-monorhizopodin, as well as the total synthesis of the former are in progress.

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, Safety of (+)-B-Methoxydiisopinocampheylborane.

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

De Joarder, Dripta published the artcileEnantioselective synthesis of a potential 1,5-syn-polyol C1-C24 subunit of (-)-caylobolide A, Safety of (+)-B-Methoxydiisopinocampheylborane, the publication is Tetrahedron Letters (2013), 54(43), 5826-5829, database is CAplus.

The synthesis of a protected possible 1,5-syn-polyol C(1)-C(24) subunit, I (TES = Et₃Si), resident in (-)-caylobolide A was accomplished. The key reaction sequence was a repetitive protocol for the construction of the syn-1,5-diol segment by Ru-catalyzed cross-metathesis and B-mediated allylation reactions.

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, Safety of (+)-B-Methoxydiisopinocampheylborane.

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

Hu, Shaojing published the artcileDiastereoselective chloroallylboration of α-chiral aldehydes, Category: ethers-buliding-blocks, the publication is Journal of Organic Chemistry (1998), 63(24), 8843-8849, database is CAplus.

Double asym. reaction of chiral (Z)-(γ-chloroallyl)diisopinocampheylboranes, d-I and l-I, with α-chiral aldehydes (S)-MeCH₂CHMeCHO, N-Boc-L-valinal (II), (R)-2,3-O-isopropylidnene-D-glyceraldehyde, and (R)- and (S)-Me₃CSiMe₂OCH₂CHMeCHO provide a new practical method for the generation of 2,3-syn-3,4-anti and 2,3-syn-3,4-syn chiral vinylchlorohydrins and vinyl epoxides. Both enantiomers d-I and l-I exhibited excellent diastereoselectivity (≥90 de) for matched cases. The mismatched cases yielded moderate to good diastereoselectivity. Thus, l-I was generated in situ from allyl chloride and l-B-methoxydiisopinocampheylborane by treatment with Li dicyclohexylamide and F₃B.OEt₂ in Et₂O/THF and reacted with II at -95° for four hours to give 60% of 99:1 mixture of vinyl chlorohydrins III and IV. Similar reaction of II with d-I gave 61% of a 15:85 mixture of III and IV. Cyclization of III in MeOH containing K₂CO₃ gave 98% vinyloxirane V.

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, Category: ethers-buliding-blocks.

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