- 3-O-Acyl triggered tandem Lewis acid catalyzed intramolecular cyclization of diacetone glucose derivatives to 5-O-acyl-3,6-anhydro-d-glucose
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BF3 mediated one-pot conversion of 3-O-acyl-d-glucose-1,2:5,6- diacetonide derivatives to 5-O-acyl-3,6-anhydro-d-glucose is described through a tandem selective intramolecular cyclization sequence.
- Bantu, Rajashaker,Mereyala, Hari Babu,Nagarapu, Lingaiah,Kantevari, Srinivas
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Read Online
- TLR7 AGONISTS
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The present invention relates to TLR7 agonists according to Formula I and their use in the treatment of diseases such as cancer and infectious disease.
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Paragraph 0167; 0171; 0172
(2021/05/28)
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- A new scalable synthesis of entecavir
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A new synthesis of entecavir from D-glucose in an average total yield of 3.5% was achieved via an intramolecular nitrile oxide cycloaddition (INOC) reaction and a Peterson olefination as key-steps. The present process was designed for industrial application, using widely available raw materials, simple and cheap reagents and avoiding low reaction temperatures, which are very common in the synthetic approaches towards similarly complex structures.
- Gioti, Efthymia G.,Koftis, Theocharis V.,Neokosmidis, Efstratios,Vastardi, Elli,Kotoulas, Stefanos S.,Trakossas, Sakellarios,Tsatsas, Theodoros,Anagnostaki, Elizabeth E.,Panagiotidis, Theodoros D.,Zacharis, Constantinos,Tolika, Evanthia P.,Varvogli, Anastasia-Aikaterini,Andreou, Thanos,Gallos, John K.
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supporting information
p. 519 - 527
(2017/12/29)
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- THE TOTAL SYNTHESIS OF GLUCOSEPANE AND COMPOUNDS OBTAINED THEREFROM
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Glucosepane is a structurally complex protein post-translational modification (PTM) believed to exist in all living organisms. Research in humans suggests that glucosepane plays a critical role in the pathophysiology of both diabetes and human aging; yet
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Page/Page column 61
(2017/04/11)
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- NOVEL 3-SUBSTITUTED 5-AMINO-6H-THIAZOLO[4,5-D]PYRIMIDINE-2,7-DIONE COMPOUNDS FOR THE TREATMENT AND PROPHYLAXIS OF VIRUS INFECTION
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The present invention relates to compounds of formula (I), wherein R1, R2 and R3 are as described herein, and their prodrugs or pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.
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Paragraph 0237; 0238; 0239
(2016/08/07)
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- Synthesis of modified Trichinella spiralis disaccharide epitopes and a comparison of their recognition by chemical mapping and saturation transfer difference NMR
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A rat monoclonal antibody 9D4 raised against the cell surface N-glycan of the parasite Trichinella spirallis protects rats against further infection. The terminal disaccharide β-d-Tyvp(1→3)β-d-GalNAcp (2) represents the immunodominant portion of the antig
- Cui, Lina,Ling, Chang-Chun,Sadowska, Joanna,Bundle, David R.
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- Reactivity of thermally treated α-dicarbonyl compounds
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The degradation reaction of thermally treated 3-deoxy-d-erythro-hexos-2- ulose and methylglyoxal, both key intermediates in Maillard chemistry, was investigated. Different analytical strategies were accomplished to cover the broad range of formed products and their different chemical behavior. These involved HPLC-DAD and accordingly LC/MS analysis of the quinoxaline derivates, GC/MS analysis of the acetylated quinoxalines, and GC-FID analysis of the decyl ester of acetic acid. As a main degradation product of 3-deoxy-d-erythro-hexos- 2-ulose, 5-(hydroxymethyl)furfural could be identified. At alkaline pH values, 3-deoxy-d-erythro-hexos-2-ulose generated various acids but no colored products. In contrast, thermal treatment of methylglyoxal yielded high molecular weight, brownish products. A dimer of methylglyoxal, first precursor for aldol-based polymerization of methylglyoxal, could be clearly identified by GC/MS.
- Pfeifer, Yvonne V.,Haase, Paul T.,Kroh, Lothar W.
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p. 3090 - 3096
(2013/08/25)
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- Asymmetric three-component domino reaction: An original access to chiral nonracemic 1,3-thiazin-2-ones
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A new asymmetric three-component domino process, based on a diastereoselective hetero-Diels-Alder reaction, involving an aldehyde, an alkene, and a chiral thiocarbamate was developed. The chiral auxiliary is directly removed during this process, leading to enantioenriched 2H-1,3-thiazin-2-ones with up to 96% ee.
- Peudru, Flavie,Le Cavelier, Fabien,Lohier, Jean-Francois,Gulea, Mihaela,Reboul, Vincent
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supporting information
p. 5710 - 5713
(2013/12/04)
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- Synthesis of (2S,4S)-4-hydroxyproline from D-glucose
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Diacetone-D-glucose 1 gives 3-O-methylxanthate 2 on reaction with NaH=Me I. Reductive deoxygenation of compound 2 by Bu3SnH gives the corresponding 3-deoxy glucose derivative 3 and on acid-catalyzed regioselective deprotection of C-5,6-acetonide gives the diol 4. The diol on oxidative cleavage with NaIO4 gives the aldehyde 5, which on further condensation with benzylamine followed by reduction with NaBH4 gives the amine 7. Z-Protection of the amine followed by methanolysis gives methyl furanoside 9. Reaction of 9 with methanesulfonyl chloride=Et3N gives the corresponding C-3-O-mesylate derivative 10. Catalytic hydrogenation of compound 10 (Pd=C=H2=MeOH 3 kg) gives bicyclic oxaazo compound 11, due to deprotection of the N-benzyl- and Z-protecting groups and intramolecular nucleophilic displacement of the C-2-O-mesylate by the C-5 amine in a one-pot reaction. Z-Protection of the amine 11 followed by acid-catalyzed hydrolysis gives acetal 13. Reduction of acetal by use of NaBH4 gives Z-prolinol 14. Selective oxidation of diol 14 by (2,2,6,6-tetramethylpiperidin-1-yl)-oxyl (TEMPO)=[(bis)(acetoxy)iodo]-benzene (BAIB) and NaClO2=NaH 2PO4, followed by Z-deprotection, gives the title compound I in 3.5% overall yield from D-glucose. Copyright Taylor & Francis Group, LLC.
- Mereyala, Hari Babu,Pathuri, Gopal,Nagarapu, Lingaiah
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p. 1278 - 1287
(2012/04/17)
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- Synthesis of locked pyranosyl nucleic acid (LpNA)
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A new locked pyranosyl nucleoside was synthesized by phenylsulfinyl- assisted chemistry. The novel building block was inserted into oligonucleotides and provides new insight on conformational restricted pyranosyl nucleosides on duplex formation
- Bomholt, Niels,Jorgensen, Per T.,Pedersen, Erik B.
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supporting information; scheme or table
p. 7376 - 7378
(2012/02/15)
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- Development of carbohydrate-derived inhibitors of acid sphingomyelinase
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The acid sphingomyelinase is an emerging drug target, especially for inflammatory lung diseases. Presently, there are no directly-acting potent inhibitors available for cell-based studies. The potent inhibitor phosphatidylinositol-3,5-bisphosphate (PtdIns3,5P2) is not only unsuited for cell culture studies, but also does not provide hints for further structural improvements. In the SAR study described here, we replaced the inositolphosphate moiety by a carbohydrate derivative and the phosphatidic acid residue by an alkylsulfone ester. The resulting compound is more active than its parent compound and offers new means for further structural modification.
- Roth, Anke G.,Redmer,Arenz, Christoph
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supporting information; experimental part
p. 939 - 944
(2010/05/02)
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- Carbanucleosides: synthesis of both enantiomers of 2-(6-chloro-purin-9-yl)-3,5-bishydroxymethyl cyclopentanol from d-glucose
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The key intermediate 1,2:5,6-di-O-isopropylidene-3-deoxy-3β-allyl-α-d-glucofuranose (8) could be conveniently prepared through radical induced allyl substitution at C-3 of appropriate 1,2:5,6-di-O-isopropylidene-α-d-glucofuranose derivatives (7a,b) and us
- Roy, Biswajit G.,Maity, Joy Krishna,Drew, Michael G.B.,Achari, Basudeb,Mandal, Sukhendu B.
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p. 8821 - 8825
(2007/10/03)
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- Facile Barton-McCombie deoxygenation of alcohols with tetrabutylammonium peroxydisulfate and formate ion
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(Chemical Equation Presented) A new method for efficient radical deoxygenation of alcohols is described for preparing bulk chemicals avoiding scale-up problems. Treatment of various thiocarbonyl derivatives with (Bu 4N)2S2O8 and HCO2Na in DMF afforded the corresponding deoxygenated products in excellent yields. The deoxygenation appears to be initiated by the transfer of a single electron to thiocarbonyl derivatives from CO2?- rather than from SO4?-.
- Hee, Sock Park,Hee, Yoon Lee,Yong, Hae Kim
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p. 3187 - 3190
(2007/10/03)
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- Synthesis of kanamycin A analogs containing a 6-amino-6-deoxyglycofuranose moiety
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Three kanamycin A analogs containing 6-amino-6-deoxyglycofuranoses have been prepared as candidates for potential activity against resistant bacteria producing 6'-N-acetyltransferase. They are 4-O-(6-amino-3,5,6-trideoxy-α-D-, -β-D-, and -β-L-erythro-hexofuranosyl)-6-O-(3-amino-3-deoxy-α-D-glucopyran osyl)-2,5-dideoxy-5-epi-5-fluorostreptamine. Structure-activity relationships of these compounds are discussed. (C) 2000 Published by Elsevier Science Ltd.
- Kobayashi, Yoshihiko,Ohgami, Tetsuro,Ohtsuki, Katsura,Tsuchiya, Tsutomu
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p. 325 - 340
(2007/10/03)
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- Total synthesis of a novel isoprostane IPF(2α)-I and its identification in biological fluids
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The first tokai synthesis of IPF(2α)-I 25 is described using D-glucose as starting material. This novel isoprostane has been used to establish its presence in human urine.
- Adiyaman, Mustafa,Lawson, John A.,Hwang, Seong-Woo,Khanapure, Subhash P.,FitzGerald, Garret A.,Rokach, Joshua
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p. 4849 - 4852
(2007/10/03)
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- Synthesis of optically active O-protected (S)- and (R)-3-hydroxyaldehydes
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(S)-3-Formyloxyaldehydes, chiral synthons for natural product synthesis were synthesized via highly stereoselective hydrogenation of the unsaturated furanose ring system derived from D-glucose or D-xylose. Alternatively, (R)-3-formyloxyaldehydes were prepared via deoxygenation of 3-hydroxyfuranoses derived from D-glucose or D-xylose.
- Kang, Suk-Ku,Cho, Hyun-Sung
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p. 367 - 370
(2007/10/02)
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- A USEFUL METHOD FOR CONVERTING 2 ALCOHOLS TO THEIR CHLORIDES WITH RETENTION OF CONFIGURATION
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Xanthate esters of 2 alcohols are converted to their chlorides with retention of configuration in good yield by use of sulfuryl chloride.
- Kozikowski, A. P.,Lee, Jaemoon
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p. 3053 - 3056
(2007/10/02)
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- USE OF O-THALLIUM(I) SALTS IN THE SYNTHESIS OF PHOSPHATE, SULFITE, AND RELATED ESTER DERIVATIVES OF CARBOHYDRATES
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O-Thallium(I) salts are shown to promote a variety of rapid, high-yield, substitution reactions at an anomeric, a primary, or a secondary position of carbohydrate derivatives.Synthesis are described of phosphates, phosphites, sulfites, and xanthic ester d
- Granata, Alessandro,Perlin, Arthur S.
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p. 165 - 172
(2007/10/02)
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- Oxidation products of arachidonic acid II. The synthesis of methyl 8R,9S,11R-trihydroxy-5Z,12E,14Z-eicosatrienoate
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A stereospecific total synthesis of the title compound, 37, starting from diacetone glucose (9), is described.Key intermediates in the synthesis are 3-deoxy-5,6-anhydro-1,2-O-isopropylidene-glucofuranose (15), obtained in 50percent yield fom 9, and methyl
- Just, George,Luthe, Corinne
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p. 1799 - 1805
(2007/10/02)
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- Process for deoxygenating secondary alcohols
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The process for removing a secondary hydroxyl group from an organic compound having at least one secondary hydroxyl group and having any amino groups protected, comprises the reaction of a reactive ester of said secondary hydroxyl group selected from the group consisting of an O-alkylthioester and an O-alkylselenoester with at least one mole of an organotin hydride, preferably tri-n-butylstannane, in an inert, aprotic solvent at a temperature of at least about 100° C and under an inert atmosphere. The process is particularly useful in removing secondary alcohols in aminoglycoside antibiotics to produce deoxy derivatives thereof having antibacterial activity. Also described are novel O-sec.-alkylthiobenzoate, O-sec.-alkyl-S-methylxanthate, N-(sec.-alkoxythiocarbonyl)-imidazole esters, and di-O-alkylthiocarbonates having at least one secondary O-alkyl group, useful intermediates of the claimed process.
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