102308-32-7Relevant articles and documents
Simple, economical and environmentally benign selective regeneration of carbonyl compounds from oximes and N,N-dimethyl hydrazones
Bose, D. Subhas,Reddy, A. V. Narsimha,Das, A. P. Rudra
, p. 1883 - 1885 (2003)
A mild, efficient, selective method for the regeneration of carbonyl compounds from oximes and N,N-dimethylhydrazones in MeCN at ambient temperature or aqueous media has been carried out in excellent yields under K 5CoW12O40·3H2O (0.01 equiv) catalysis.
A stereoselective synthesis of sphingosine, a protein kinase C inhibitor
Nimkar,Menaldino,Merrill,Liotta
, p. 3037 - 3040 (1988)
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STEREOCONTROLLED ADDITION TO A PENALDIC ACID EQUIVALENT: AN ASYMMETRIC SYNTHESIS OF THREO-β-HYDROXY-L-GLUTAMIC ACID
Garner, Philip
, p. 5855 - 5858 (1984)
The asymmetric synthesis of threo-β-hydroxy-L-glutamic acid (7) via a stereoselective addition to the chiral penaldic acid equivalent 3 is described.
Synthesis and immobilization of ceramide analogs on silica particles
Yin, Jianming,Liu, Hanlan,Pidgeon, Charles
, p. 179 - 182 (1998)
Ceramides are the major lipid components of the stratum corneum, the major permeability barrier of the skin. Here we report a chemical synthesis of ceramide analogs covalently bonded on the silica particles, that can be used to predict the skin permeability of chemicals via HPLC methods.
β-isocupreidine-catalyzed Baylis-Hillman reaction of chiral N-Boc-α-amino aldehydes
Nakano, Ayako,Takahashi, Keisuke,Ishihara, Jun,Hatakeyama, Susumi
, p. 5357 - 5360 (2006)
β-Isocupreidine (β-ICD)-catalyzed Baylis-Hillman reaction of chiral N-Boc-α-amino aldehydes and 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) takes place without racemization and exhibits the match-mismatch relationship between the substrate and the catalyst. In the case of acyclic amino aldehydes, α,-substrates show excellent syn selectivity and high reactivity in contrast to L-substrates. On the other hand, in the case of cyclic amino aldehydes, D-substrates rather than L-substrates show excellent anti selectivity and high reactivity.
Wet silica-supported permanganate for the cleavage of semicarbazones and phenylhydrazones under solvent-free conditions
Hajipour, Abdol R.,Adibi, Hadi,Ruoho, Arnold E.
, p. 4553 - 4555 (2003)
Wet silica-supported potassium permanganate was used as an inexpensive and efficient reagent for conversion of semicarbazones and phenylhydrazones to the corresponding carbonyl compounds under solid-state conditions.
A straightforward synthesis of N-BOC-L-serinal and N-BOC-L-threoninal acetonides
Meffre,Durand,Branquet,Le Goffic
, p. 2147 - 2152 (1994)
An improved procedure for the synthesis of optically active N-tert- butoxycarbonyl L-serinal acetonide and threoninal analogue from ester precursors is described.
N-AS-triggered SPMs are direct regulators of microglia in a model of Alzheimer’s disease
Bae, Jae-sung,Choi, Min-Koo,Han, Seung Hoon,Jin, Hee Kyung,Kim, Hee-Jin,Kim, Seung Hyun,Lee, Ju Youn,Park, Cheol-Min,Park, Min Hee,Schuchman, Edward H.,Song, Im-Sook,Yu, Eunsoo
, (2020)
Sphingosine kinase1 (SphK1) is an acetyl-CoA dependent acetyltransferase which acts on cyclooxygenase2 (COX2) in neurons in a model of Alzheimer’s disease (AD). However, the mechanism underlying this activity was unexplored. Here we show that N-acetyl sphingosine (N-AS) is first generated by acetyl-CoA and sphingosine through SphK1. N-AS then acetylates serine 565 (S565) of COX2, and the N-AS-acetylated COX2 induces the production of specialized pro-resolving mediators (SPMs). In a mouse model of AD, microglia show a reduction in N-AS generation, leading to decreased acetyl-S565 COX2 and SPM production. Treatment with N-AS increases acetylated COX2 and N-AS-triggered SPMs in microglia of AD mice, leading to resolution of neuroinflammation, an increase in microglial phagocytosis, and improved memory. Taken together, these results identify a role of N-AS in the dysfunction of microglia in AD.
An Expedient Total Synthesis of Chivosazole F: an Actin-Binding Antimitotic Macrolide from the Myxobacterium Sorangium Cellulosum
Williams, Simon,Jin, Jialu,Kan, S. B. Jennifer,Li, Mungyuen,Gibson, Lisa J.,Paterson, Ian
, p. 645 - 649 (2017)
A unified strategy for the chemical synthesis of the chivosazoles is described. This strategy is based on two closely related approaches involving the late-stage installation of the isomerization-prone (2Z,4E,6Z,8E)-tetraenoate motif, and an expedient fra
Late-Stage Intermolecular Allylic C-H Amination
Clark, Joseph R.,Dixon, Charlie F.,Feng, Kaibo,Han, Wei,Ide, Takafumi,Koch, Vanessa,Teng, Dawei,Wendell, Chloe I.,White, M. Christina
supporting information, p. 14969 - 14975 (2021/10/01)
Allylic amination enables late-stage functionalization of natural products where allylic C-H bonds are abundant and introduction of nitrogen may alter biological profiles. Despite advances, intermolecular allylic amination remains a challenging problem due to reactivity and selectivity issues that often mandate excess substrate, furnish product mixtures, and render important classes of olefins (for example, functionalized cyclic) not viable substrates. Here we report that a sustainable manganese perchlorophthalocyanine catalyst, [MnIII(ClPc)], achieves selective, preparative intermolecular allylic C-H amination of 32 cyclic and linear compounds, including ones housing basic amines and competing sites for allylic, ethereal, and benzylic amination. Mechanistic studies support that the high selectivity of [MnIII(ClPc)] may be attributed to its electrophilic, bulky nature and stepwise amination mechanism. Late-stage amination is demonstrated on five distinct classes of natural products, generally with >20:1 site-, regio-, and diastereoselectivity.
