- Synthesis of an (R)-Garner-type aldehyde from L-serine: Useful building block for a (+)-furanomycin derivative
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(+)-Furanomycin is an antibiotic that substitutes for L-isoleucine in bacterial protein translation. We propose here a new short synthesis of a useful intermediate, a 1,2-diprotected 2-aminopent-4-ene-1,3-diol, starting from the inexpensive natural amino acid L-serine, and via a Garner-type aldehyde. The (R)-α-amino aldehyde was obtained by the construction of an oxazoline ring between the N-protected amino group and the hydroxy group that resulted from reduction of the carboxylic acid functionality of L-serine. Georg Thieme Verlag Stuttgart.
- Bartoli, Giuseppe,Di Antonio, Giustino,Fiocchi, Roberto,Giuli, Sandra,Marcantoni, Enrico,Marcolini, Mauro
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- Simple molecular engineering of glycol nucleic acid: Progression from self-pairing to cross-pairing with cDNA and RNA
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The acyclic chiral nucleic acid analogue, Glycol Nucleic Acid (GNA), displayed exceptional structural simplicity and atom economy while forming self-paired duplexes, using canonical Watson-Crick base pairing. We disclose here that the replacement of phosp
- Bose, Tanaya,Kumar, Vaijayanti A.
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Read Online
- Application of the highly sensitive labeling reagent to the structural confirmation of readily isomerizable peptides
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Thioamycolamide A (1) is a biosynthetically unique cytotoxic cyclic microbial lipopeptide that bears a d-configured thiazoline, a thioether bridge, a fatty acid side chain, and a reduced C-terminus. It has gained attention for its unique structure, and very recently we reported the total synthesis of 1 via a biomimetic route. The NMR spectra of synthetic 1 agreed with those of natural 1. However, structural identity between peptidic natural and synthetic compounds is often difficult to confirm by comparison of NMR spectra because their NMR spectra vary depending on the conditions in the NMR tube, which often result in the structural misassignment of peptidic compounds. Especially, our total synthesis based on the putative biomimetic route potentially gives 1 as a diastereomixture at the final step. The problem is that the diastereomers of peptidic mid-sized molecules often exhibit similar properties (such as NMR spectra and bioactivities), and their separation procedures are often laborious. Herein we report the structural confirmation of synthetic 1 by the LC–MS-based chromatographic comparison with the use of our highly sensitive labeling reagent l-FDVDA; the highly sensitive-advanced Marfey’s method (HS-advanced Marfey’s method). This work demonstrated the utility of our highly sensitive labeling reagent for the structural determination of not only scarce natural products but also readily isomerizable synthetic compounds.
- Pan, Chengqian,Kuranaga, Takefumi,Kakeya, Hideaki
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- COMPOUNDS FOR TREATING FAMILIAL DYSAUTONOMIA
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The present description relates to compounds useful for improving pre-mRNA splicing in a cell. In particular, another aspect of the present description relates to substituted thieno [3,2-d]pyrimidine compounds, forms, and pharmaceutical compositions there
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Page/Page column 65-66
(2021/06/22)
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- CYCLIC COMPOUNDS AND METHODS OF USING SAME
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The present application relates to compounds of Formula (I), as defined herein, and pharmaceutically acceptable salts thereof. The present application also describes pharmaceutical composition comprising a compound of Formula (I), and pharmaceutically acc
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Page/Page column 203
(2021/06/11)
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- THIOENO[3,2-B] PYRIDIN-7-AMINE COMPOUNDS FOR TREATING FAMILIAL DYSAUTONOMIA
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The present description relates'to compounds of formula (I) useful for improving pre-mRNA splicing in a cell. In particular, another aspect of the present description relates to substituted thieno[3,2-b]pyridine compounds, forms, and pharmaceutical compos
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Page/Page column 71; 72
(2020/08/28)
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- MACROCYCLIC KINASE INHIBITORS AND THEIR USE
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The present disclosure relates to certain chiral diaryl macrocyclic derivatives, pharmaceutical compositions containing them, and methods of using them to treat cancer, pain, neurological diseases, autoimmune diseases, and inflammation.
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Paragraph 0437; 0440
(2019/07/13)
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- PROCESS FOR PREPARATION OF SACUBUTRIL INTERMEDIATE
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The present application relates to a process for preparation of tert-butyl (R)-(1-([1,1'-biphenyl]-4- yl)-3-hydroxypropan-2-yl)carbamate (IA). The compound of formula (IA) may be used as an intermediate for the preparation of sacubitril.
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Page/Page column 27
(2017/12/29)
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- Morita-Baylis-Hillman approach toward formal total synthesis of tamiflu and total synthesis of gabaculine
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A Morita-Baylis-Hillman reaction mediated approach to the formal total synthesis of oseltamivir and the total synthesis of gabaculine is described. This strategy involves the enantiocontrolled preparation of Corey's intermediate in 22 % yield, which is pr
- Bhowmik, Subhendu,Batra, Sanjay
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p. 7145 - 7151
(2013/11/06)
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- A stereodivergent route to four stereoisomeric 3′- acetoxycyclopentenylglycine derivatives
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A short and efficient synthetic route to four stereoisomeric 3-acetoxycyclopentenylglycine derivatives from l-serine has been developed. The method features a stereoselective conjugate addition and ring-closing metathesis as key steps. Georg Thieme Verlag Stuttgart · New York.
- Kundu, Indranil,Maitra, Ratnava,Jana, Manoranjan,Chattopadhyay, Shital K.
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experimental part
p. 304 - 310
(2012/03/26)
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- Development of a scalable chiral synthesis of MK-3281, an inhibitor of the hepatitis C virus NS5B polymerase
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The development of a scalable chiral synthesis for the HCV NS5B inhibitor MK-3281 is being reported. Several alternative routes were explored and are being described. Georg Thieme Verlag Stuttgart ? New York.
- Colarusso, Stefania,Conte, Immacolata,Di Filippo, Marcello,Ercolani, Caterina,MacKay, Angela C.,Palumbi, Maria Cecilia,Rico Ferreira, Maria Del Rosario,Stansfield, Ian,Zaramella, Simone,Narjes, Frank,Habermann, J?rg
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experimental part
p. 1527 - 1532
(2011/08/03)
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- Efficient synthesis of a configurationally stable L-serinal derivative
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An efficient synthesis of a configurationally stable L-serinal derivative 8 was achieved using an N-hydroxymethyl group in about 50% overall yield in four steps from L-serine. Not more than 1% racemization was observed during the preparation of 8. Its enantiomeric integrity was maintained for at least 15 days at room temperature, and it was stable on silica gel. The orthogonal protective groups of 8 would make it a useful chiral synthon.
- Yoo, Dongwon,Seok Oh, Joon,Lee, Dong-Whal,Kim, Young Gyu
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p. 2979 - 2982
(2007/10/03)
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- Effective and mild method for preparation of optically active α-amino aldehydes via TEMPO oxidation
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The TEMPO oxidation method is successfully applied to preparation of variously protected, optically active α-amino aldehydes without racemization and in very good yield.
- Jurczak, Janusz,Gryko, Dorota,Kobrzycka, Elzbieta,Gruza, Henryk,Prokopowicz, Piotr
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p. 6051 - 6064
(2007/10/03)
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- Facile synthesis of D-amino acids from an L-serine-derived aziridine
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Using the concept that L-serine can be converted into a desymmetrized γ-diol derivative, five D-amino acids were synthesized from a common aziridine intermediate by a general, high-yielding three-step process. The key 2-t-butyldimethylsiloxymethyl N-t-butoxycarbonyl aziridine intermediate was synthesized in four steps and 65% overall yield.
- Travins, Jeremy M.,Etzkorn, Felicia A.
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p. 9389 - 9392
(2007/10/03)
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- Diastereoselective synthesis of 1,2-diamines by palladium catalyzed aza-Claisen rearrangement
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In the thermal rearrangement of allylic trichloroacetimidates 6, no 1,2-asymmetric induction can be observed. Palladium(II) catalyzed, hoever, the rearrangement takes place at 25°C and yields diastereoselective (de ≥ 98%) the anti-1,2-diamines 7. The ally
- Gonda,Helland,Ernst,Bellus
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p. 729 - 733
(2007/10/02)
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