3067-56-9Relevant articles and documents
Method for preparing eribulin dehydroxylation intermediate by one-pot method
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Paragraph 0025-0026, (2021/09/08)
The invention relates to the technical field of organic synthesis, in particular to a method for preparing an eribulin dehydroxylation intermediate by a one-pot method, which comprises the following steps of in an organic solvent, taking a compound I as a raw material, carrying out oxidation-reduction reaction on the compound I, a reducing agent, a catalyst and alkali, and separating and purifying reaction liquid to obtain a compound as shown in a formula II, namely the eribulin dehydroxylation intermediate. According to the method disclosed by the invention, sulfonyl chloride, Pd/C, iodine elementary substance and pyridine which are not green and are high in price are not used, but cheap and green reagents are adopted for replacement, so that the greenness, the economical efficiency and the safety of the reaction are remarkably improved. The reaction efficiency is greatly improved and the reaction cost is reduced by shortening the reaction steps and the reaction time.
INTERMEDIATES FOR THE PREPARATION OF ERIBULIN THEREOF
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Page/Page column 8, (2019/06/11)
The present invention relates to novel intermediates of Eribulin and process for the preparation of the same. The process of the present invention is commercially viable and can be easily adopted for plant scale operations. The present invention relates to tetrahydrofuran compounds of formula I, X, XI, D and B.
Synthesis of 1,3,4,6-Tetra-O-acetyl-l-gulose
Che, Rui,Liu, Xingui,Lu, Wei
, p. 237 - 241 (2017/03/05)
A novel, practical and concise synthesis of 1,3,4,6-tetra-O-acetyl-l-gulose is described, using d-glucuronolactone as the starting material and other inexpensive and readily available agents (22% overall yield in 9 steps). With this method, the synthesis of l-gulose and the tumor-targeting disaccharide of BLMs can be more efficient and convenient.
Attempted synthesis of the imidazylate of an α-hydroxylactone results in unexpected chlorination: Synthesis and X-ray crystal structure of 5-Chloro-5-deoxy-1,2- O -isopropylidene-β- l -idurono-6,3-lactone
Mohamed, Shifaza,Bernhardt, Paul V.,Ferro, Vito
, p. 197 - 205 (2014/06/09)
Attempted synthesis of the imidazylate derivative of 1,2-O-isopropylidene- α-D-glucurono-6,3-lactone (2) via treatment with sulfuryl chloride in the presence of excess imidazole in DMF at either -40°C or -70°C resulted in the unexpected formation of 5-chloro-5-deoxy-1,2-O-isopropylidene-β-l- idurono-6,3-lactone (7). Chloride 7 presumably forms via the rapid S N2 displacement by a chloride ion of an initially formed chlorosulfate ester intermediate, which is evidently unusually reactive. The identity of the product was confirmed by a single-crystal X-ray structure determination. Taylor & Francis Group, LLC.
Synthesis of purine nucleosides from D -glucuronic acid derivatives and evaluation of their cholinesterase-inhibitory activities
Xavier, Nuno M.,Schwarz, Stefan,Vaz, Pedro D.,Csuk, Rene,Rauter, Amelia P.
, p. 2770 - 2779 (2014/05/06)
Glucuronolactones were used as precursors for N9 and N 7 purine nucleosides containing glucuronic acid derivatives in their structures. Acetylated N-benzylglucofuran- and glucopyranuronamides were synthesized in a few steps from glucofuranurono-6,3-lactone. They were converted into the corresponding furanosyl and pyranosyl uronamide-based nucleosides by N-glycosylation with silylated 2-acetamido-6-chloropurine in the presence of trimethylsilyl triflate. The triacetylated bicyclic lactone was coupled itself with the nucleobase to give bicyclic N9,N7 nucleosides. Tri-O-acetylglucopyranurono-6,1-lactone was used for the first time as a glycosyl donor for N-glycosylation, and led to β-configured N9- and N7-linked purinylglucuronides under reaction conditions similar to those used with the 1-O-acetyl-substituted glycosyl donors. The cholinesterase inhibitory profiles of the synthetic nucleosides bearing glucuronic acid derivatives as glycons were evaluated, and they showed moderate selective acetylcholinesterase inhibitory activities (Ki = 14.78-50.53 μM). The best inhibition was shown by the furanosyl N 9-linked uronamide-based purine nucleoside. The synthesis of furanosyl and pyranosyl N9 and N7 purine nucleosides containing glucofuranurono-6,3-lactone, N-benzylglucuronamide, and glucuronic acid moieties is reported. Glucuronolactones were used as glycosyl donors or converted into suitable 1-O-acetyl derivatives for purine glycosylation. Some nucleosides showed moderate and selective inhibition of acetylcholinesterase. Copyright
Synthetic 1-deoxynojirimycin N-substituted peptides offer prolonged disruption to N-linked glycan processing
Aguilar, Aim Lpez,Escribano, Jaime,Wentworth, Paul,Butters, Terry D.
supporting information, p. 2809 - 2813 (2015/02/02)
A panel of 1-deoxynojirimycin (DNJ) N-linked peptides were synthesized. Their IC50 values were measured in vitro against a-glucosidases I and II and were found to be in the micromolar range for both isozymes, and better than that of the iminosugar NB-DNJ (miglustat, 3) against a-glucosidase II. Cell-based studies revealed that although the free iminosugar 3 is most effective at disrupting N-linked glycan processing for shortterm incubations (one day), when the cell-based studies were extended to three days, the DNJ N-linked tetrapeptide KDEL, which is an endoplasmic reticulum (ER)-retaining sequence, performed far better than 3. In low inhibitor washout studies, NB-DNJ inhibition was decreased to zero after 24 h, but DNJ- KDEL retained 13% activity. This method offers a general approach for targeting drugs to the ER and prolonging their activity. Moreover, it is modular, so as new iminosugars of increased potency are discovered, they can be added to this template for targeting.
Process development of halaven: Synthesis of the C14-C35 fragment via iterative nozaki-hiyama-kishi reaction-williamson ether cyclization
Austad, Brian C.,Benayoud, Farid,Calkins, Trevor L.,Campagna, Silvio,Chase, Charles E.,Choi, Hyeong-Wook,Christ, William,Costanzo, Robert,Cutter, James,Endo, Atsushi,Fang, Francis G.,Hu, Yongbo,Lewis, Bryan M.,Lewis, Michael D.,McKenna, Shawn,Noland, Thomas A.,Orr, John D.,Pesant, Marc,Schnaderbeck, Matthew J.,Wilkie, Gordon D.,Abe, Taichi,Asai, Naoki,Asai, Yumi,Kayano, Akio,Kimoto, Yuichi,Komatsu, Yuki,Kubota, Manabu,Kuroda, Hirofumi,Mizuno, Masanori,Nakamura, Taiju,Omae, Takao,Ozeki, Naoki,Suzuki, Taeko,Takigawa, Teiji,Watanabe, Tomohiro,Yoshizawa, Kazuhiro
, p. 327 - 332 (2013/04/10)
Multikilogram manufacturing process of the Halaven C14-C35 fragment is described. The synthesis features convergent assembly of subunits by iterative asymmetric Ni/Cr-mediated coupling executed in fixed equipment. Georg Thieme Verlag Stuttgart - New York.
Scalable syntheses of both enantiomers of DNJNAc and DGJNAc from glucuronolactone: The effect of N-alkylation on hexosaminidase inhibition
Glawar, Andreas F. G.,Best, Daniel,Ayers, Benjamin J.,Miyauchi, Saori,Nakagawa, Shinpei,Aguilar-Moncayo, Matilde,García Fernández, José M.,Ortiz Mellet, Carmen,Crabtree, Elizabeth V.,Butters, Terry D.,Wilson, Francis X.,Kato, Atsushi,Fleet, George W. J.
experimental part, p. 9341 - 9359 (2012/09/22)
The efficient scalable syntheses of 2-acetamido-1,2-dideoxy-D-galacto- nojirimycin (DGJNAc) and 2-acetamido-1,2-dideoxy-D-gluco-nojirimycin (DNJNAc) from D-glucuronolactone, as well as of their enantiomers from L-glucuronolactone, are reported. The evaluation of both enantiomers of DNJNAc and DGJNAc, along with their N-alkyl derivatives, as glycosidase inhibitors showed that DGJNAc and its N-alkyl derivatives were all inhibitors of α-GalNAcase but that none of the epimeric DNJNAc derivatives inhibited this enzyme. In contrast, both DGJNAc and DNJNAc, as well as their alkyl derivatives, were potent inhibitors of β-GlcNAcases and β-GalNAcases. Neither of the L-enantiomers showed any significant inhibition of any of the enzymes tested. Correlation of the in vitro inhibition with the cellular data, by using a free oligosaccharide analysis of the lysosomal enzyme inhibition, revealed the following structure-property relationship: hydrophobic side-chains preferentially promoted the intracellular access of iminosugars to those inhibitors with more-hydrophilic side-chain characteristics. Getting the NAc of it: Scalable syntheses of DGJNAc and DNJNAc from D-glucuronolactone are reported. DGJNAc and its N-alkyl derivatives were inhibitors of α-GalNAcase and both DGJNAc and DNJNAc were potent inhibitors of β-GlcNAcases and β-GalNAcases. Copyright
First total synthesis and absolute stereochemical assignment of vittarilide-A, an antioxidant extractive component isolated from Vittaria anguste-elongata Hayata
Takahashi, Masaki,Murata, Yusuke,Hakamata, Yuki,Suzuki, Kohei,Sengoku, Tetsuya,Yoda, Hidemi
scheme or table, p. 7997 - 8002 (2012/09/25)
The first stereocontrolled synthesis of vittarilide-A and its C5-epimer was completed from d-glucuronolactone. Comparison with the spectroscopic properties reported for authentic material has given a clear indication as to the absolute stereochemistry of the natural vittarilide-A.
Design and synthesis by click triazole formation of paclitaxel mimics with simplified core and side-chain structures
Manach, Claire Le,Baron, Aurélie,Guillot, Régis,Vauzeilles, Boris,Beau, Jean-Marie
scheme or table, p. 1462 - 1465 (2011/06/10)
A library of paclitaxel (taxol) mimics was obtained by a straightforward strategy involving rational design and an efficient synthesis of a simplified taxane core substitute, together with a click-chemistry combinatorial search for phenylisoserine side-chain surrogates.