- Method for synthesizing release type xylose ester perfume for tobacco perfuming
-
A synthesis method of a release type xylose ester spice for flavoring tobacco is provided. The glucose is used as a raw material, the principle of esterifying carboxylic acid and alcohol to prepare ester is adopted, a common parent carboxylic acid which c
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-
-
- Nitrosocarbonyl Carbohydrate Derivatives: Hetero Diels-Alder and Ene Reaction Products for Useful Organic Synthesis
-
The generation and trapping of two new nitrosocarbonyl intermediates bearing carbohydrate-based chiral substituents is achieved by the mild oxidation of the corresponding nitrile oxides with tertiary amine N -oxides. Their capture with suitable dienes and alkenes afforded the corresponding hetero Diels-Alder cycloadducts and ene adducts from fair to excellent yields. The entire methodology looks highly promising by the easy conversion of aldoximes into hydroxymoyl halides, widening the access to nitrosocarbonyls, versatile tools in organic synthesis.
- Corti, Marco,Leusciatti, Marco,Moiola, Mattia,Mella, Mariella,Quadrelli, Paolo
-
p. 574 - 586
(2020/10/06)
-
- Synthesis and Glycosylation Properties of C6-Silylated Ido- and Gluco-Pyranosyl Donors
-
Silyl groups are widely used as alcohol protecting groups and their study has provided insight on some very remarkable structure and reactivity features within carbohydrate chemistry. However, not much work has been put into the effect on the reactivity of silyl groups directly attached to the sugar carbon chain. In this work, we have developed a synthetic methodology to obtain both d-glucosyl and l-idosyl donors containing a dimethylphenylsilyl group directly attached to C6. Glycosylation and competition experiments with different glycosyl acceptors have shown that this group is completely stable under glycosylation conditions and enhances reactivity beyond what a benzyl group attached to the sugar oxygen would do. Finally, we found adequate conditions for the protodesilylation of Si-containing glycosides to yield the 6-deoxy sugar analog.
- álvarez-Martínez, Ignacio,Pedersen, Christian Marcus
-
-
- Metal-free [3+2] cycloaddition of glycosyl olefinic ester with in situ generated CF3CHN2: Access to CF3-substituted pyrazoline glycoconjugates
-
An efficient [3 + 2] cycloaddition of glycosyl olefinic ester with in situ generated CF3CHN2 for the syntheses of CF3-substituted pyrazoline glycoconjugate has been developed. This mild, one-pot reaction condition avoiding the use of metallic catalyst and additive will be useful in the pharmaceutical industry. This reaction features are the broad substrate scope, good functional group tolerance with good to high yields.
- Javed,mandal, Pintu Kumar
-
-
- N-Alkylated C-Glycosyl Amino Acid Derivatives: Synthesis by a One-Pot Four-Component Ugi Reaction
-
C-glycosides represent an important group of naturally occurring glycosylation derivatives but are also efficient mimetics of native O-glycosides. Here, a one-pot four-component methodology is described toward a library of N-alkylated C-glycosyl amino acid derivatives comprising seven different isopropylidene-protected carbohydrate units. The applied methodology tolerates different amines and isocyanides and provides access to Ugi products in yields up to 85 %. X-ray analysis of selected products bearing three different carbohydrate motifs and comparison of their crystal structures with similar ones deposited in Cambridge Crystallographic Database revealed that four structures adopt different conformations, mostly not typical for peptide structures. This property opens the possibility to exploit here described N-alkylated C-glycosyl amino acid derivatives as templates to access different biotic and abiotic secondary structures.
- ?tefani?, Zoran,Jeri?, Ivanka,Vazdar, Katarina,Vlahovi?ek-Kahlina, Kristina
-
p. 838 - 844
(2020/06/02)
-
- MODIFIED NUCLEOSIDE PHOSPHORAMIDITES
-
The present disclosure relates to compounds and compositions containing 5'-phosphoramidite nucleoside monomers of formulae (I) and (II), and methods of making and use, wherein the substituents are as defined in the appended claims.
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-
- Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands
-
Glycosyl triazoles are conveniently accessible and contain multiple metal-binding units that may assist in metal-mediated catalysis. Azide derivatives of d-glucose have been converted to their respective aryltriazoles and screened as ligands for the synthesis of 2-substituted benz-fused azoles and benzimidazoquinazolinones by Cu-catalyzed intramolecular Ullmann type C-heteroatom coupling. Good to excellent yields for a variety of benz-fused heterocyles were obtained for this readily accessible catalytic system.
- Mishra, Nidhi,Singh, Anoop S.,Agrahari, Anand K.,Singh, Sumit K.,Singh, Mala,Tiwari, Vinod K.
-
p. 389 - 399
(2019/05/06)
-
- I2/PPh3-mediated facile synthesis of glycoconjugated N-acylbenzotriazoles
-
A well-stabilized method for synthesis of N-acylbenzotriazoles from carboxylic acids using I2/PPh3 in anhydrous dichloromethane has been extended in glycochemistry to synthesize glycoconjugated N-acylbenzotriazoles with high yields at room temperature in 2-hour reaction time.
- Singh, Mala,Agrahari, Anand K.,Mishra, Nidhi,Singh, Anoop S.,Tiwari, Vinod K.
-
p. 125 - 132
(2018/09/14)
-
- Synthesis and antiplasmodial activity of purine-based C-nucleoside analogues
-
A series of homologous C-nucleoside mimics have been synthesized via an efficient and facile synthetic protocol involving the conjugate addition of purine to sugar derived olefinic ester in good yields. The synthesized compounds were evaluated for their a
- Singh, Kartikey,Joshi, Prince,Mahar, Rohit,Baranwal, Pragati,Shukla, Sanjeev K.,Tripathi, Renu,Tripathi, Rama Pati
-
p. 1232 - 1238
(2018/08/01)
-
- Furanosyl Nucleoside Analogues Embodying Triazole or Theobromine Units as Potential Lead Molecules for Alzheimer's Disease
-
The synthesis of novel types of furanosyl nucleoside analogues, namely N-(benzyltriazolyl)methyl glucuronamide derivatives, N-dodecyl glucuronamide-based phenyltriazole nucleosides, and theobromine xylosyl 5′-isonucleosides, as potential cholinesterase in
- Gon?alves-Pereira, Rita,Pereira, Margarida P.,Serra, Sofia G.,Loesche, Anne,Csuk, René,Silvestre, Samuel,Costa, Paulo J.,Oliveira, M. Concei??o,Xavier, Nuno M.
-
p. 2667 - 2681
(2018/06/11)
-
- Furan glucosyl triazole type compound and preparation method and bactericide thereof
-
The invention relates to the field of bactericidal compounds, in particular to a furan glucosyl triazole type compound and a preparation and a bactericide thereof. The molecular formula of the furan glucosyl triazole type compound is shown in the following description, wherein R1 is methyl or benzyl, and R2 are phenyl and derivative of the phenyl or ethyl derivatives. Based on structural characteristics of the substrate fructose-6-phosphate and an ISOM catalytic hypothesis mechanism, the inventor adopts a five-membered furan glucose derivative with a similar structure as a basic skeleton, introduces an effective active group triazole structure of pesticides, designs a series of novel furan glucosyl triazole type compounds for the first time, studies the biological activities of the furan glucosyl triazole type compound, examines structure-activity relationships of the furan glucosyl triazole type compound, and lays the foundation for selecting better inhibitors.
- -
-
Paragraph 0057; 0076-0078
(2018/04/21)
-
- Total synthesis of cephalosporolide E via a tandem radical/polar crossover reaction. The use of the radical cations under nonoxidative conditions in total synthesis
-
The present work reports the first example of the use of the chemistry of radical cations under nonoxidative conditions in total synthesis. Using a late-stage tandem radical/polar crossover reaction, a highly stereoselective total synthesis of cephalospor
- Cortezano-Arellano, Omar,Quintero, Leticia,Sartillo-Piscil, Fernando
-
p. 2601 - 2608
(2015/03/18)
-
- Formal synthesis of a disaccharide repeating unit (IdoA-GlcN) of heparin and heparan sulfate
-
A concise route to access the key disaccharide repeating unit (IdoA-GlcN) of heparan sulfate is described. The synthesis was accomplished by commercially available diacetone α-d-glucose to functional group transformations, which led to the formation of a
- Sawant, Ratnnadeep C.,Liao, Ying-Ju,Lin, Yi-Jyun,Badsara, Satpal Singh,Luo, Shun-Yuan
-
p. 19027 - 19033
(2015/06/09)
-
- Titanocene dihalides and ferrocenes bearing a pendant α-d- xylofuranos-5-yl or α-d-ribofuranos-5-yl moiety. synthesis, characterization, and cytotoxic activity
-
Titanocene dichlorides of general formula [(η5-C 5H5)(η5-C5H4R) TiCl2] (where R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl-α- d-xylofuranos-5-yl (Xylf) (8a); R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl- α-d-ribofuranos-5-yl (Ribf) (8b)) and [(η5-C 5H4R)2TiCl2] (R = Xylf (9a); R = Ribf (9b)) were prepared by reaction of the corresponding lithium cyclopentadienides 7a,b with an equimolar amount of [(η5-C 5H5)TiCl3] or a 0.5 mol amount of [TiCl 4(THF)2]. Titanocene difluorides of the general formula [(η5-C5H4R1)(η5- C5H4R2)TiF2] (R1 = H and R2 = Ribf (10); R1 = R2 = Xylf (11a); R 1 = R2 = Ribf (11b)) were obtained by fluorination of the corresponding titanocene dichlorides 8b and 9 with the fluorinating agent {2-(CH2NMe2)C6H4-κC,N}(n-Bu) 2SnF in high yields. Alternatively, complexes 11 were prepared in a straightforward way by direct reaction of [TiF4(THF)2] with 2 equiv of the corresponding lithium cyclopentadienide 7a,b. Ferrocene complexes [(η5-C5H4R)2Fe] (R = Xylf (12a); R = Ribf (12b)) were synthesized by metathesis of 2 equiv of lithium cyclopentadienide 7a,b and 1 equiv of anhydrous FeCl2. Deprotection of the benzyl group in ferrocenes 12 proceeded cleanly by a catalytic hydrogenation on Pd/C and afforded the ferrocene diols [(η5- C5H4R)2Fe] (R = 5-deoxy-1,2-di-O- isopropylidene-α-d-xylofuranos-5-yl (Xylf-OH) (14a); R = 5-deoxy-1,2-di-O-isopropylidene-α-d-ribofuranos-5-yl (Ribf-OH) (14b)). A scaled up benzyl deprotection with Et3SiH as a hydrogen source led to the replacement of only one benzyl group, which gave the ferrocene alcohol [(η5-C5H4R1)(η5- C5H4R2)Fe] (R1 = Xylf and R 2 = Xylf-OH (13)). The prepared complexes were characterized by elemental analysis, melting point determination, NMR, IR, and ESI-MS, and the molecular structure of 9b was determined by X-ray diffraction analysis. The cytotoxic activity of complexes 8-14 against A2780 and A2780cis cancer cells was evaluated by MTT tests. Titanocene difluorides 10 and 11 and ferrocene diol 14a showed cytotoxicity against A2780 cells in the medium to low micromolar range, while the most active species, 11b, displayed about 40% higher cytotoxicity against A2780cis in comparison to a cisplatin standard.
- Hodik, Tomas,Lamac, Martin,Cervenkova St'Astna, Lucie,Karban, Jindrich,Koubkova, Lucie,Hrstka, Roman,Cisarova, Ivana,Pinkas, Jiri
-
p. 2059 - 2070
(2014/05/20)
-
- Studies towards the total synthesis of hygrocins A and B
-
The western segment of hygrocins A-B has been synthesized through the coupling of a chiral C5-C13 synthon with the sterically demanding hexasubstituted naphthalenic core. The C5-C13 chiral fragment has been assembled via a stereoselective Johnson orthoest
- Rasapalli, Sivappa,Jarugumilli, Gopalakrishna,Yarrapothu, Gangadhara Rao,Ijaz, Hamza,Golen, James A.,Williard, Paul G.
-
p. 821 - 825
(2014/02/14)
-
- Conformationally constrained goniofufurone mimics as inhibitors of tumour cells growth: Design, synthesis and SAR study
-
Synthesis of conformationally restricted (+)-goniofufurone (1) and 7-epi-(+)-goniofufurone (2) analogues, with embedded O-isopropylidene, O-methylidene or cyclic carbonate functions is disclosed starting from d-glucose. A number of potential bioisosteres
- Benedekovi?, Goran,Francuz, Jovana,Kova?evi?, Ivana,Popsavin, Mirjana,Sre?o Zelenovi?, Bojana,Koji?, Vesna,Bogdanovi?, Gordana,Divjakovi?, Vladimir,Popsavin, Velimir
-
supporting information
p. 449 - 458
(2014/07/07)
-
- TRICYCLIC NUCLEIC ACID ANALOGS
-
The present disclosure provides tricyclic nucleosides and oligomeric compounds prepared therefrom. The tricyclic nucleosides each have a tricyclic ribosyl sugar moiety wherein a bridge between the 2' and 4' ribosyl ring carbon atoms further comprises a fused carbocyclic or heterocyclic ring. The tricyclic nucleosides are expected to be useful for enhancing properties of oligomeric compounds including for example binding affinity and nuclease resistance.
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-
Page/Page column 68
(2013/11/05)
-
- Studies toward total synthesis of divergolides C and D
-
A facile synthesis of the western segment of divergolides C and D has been developed. Exploratory studies with two disconnections, i.e., C4-C5 vs C5-C6, for elaboration of the ansa bridge to the sterically demanding hexasubstituted naphthalenic aromatic c
- Rasapalli, Sivappa,Jarugumilli, Gopalakrishna,Yarrapothu, Gangadhara Rao,Golen, James A.,Rheingold, Arnold L.
-
p. 1736 - 1739
(2013/06/26)
-
- Regioselective epoxide opening of epoxyamides derived from d-glucose. Cyclization approaches to azepanes
-
Epoxyamides obtained from d-glucose have been evaluated as tools to obtain polyhydroxyazepanes. The stereoselectivity in formation of the epoxyamides was proven to be dependent of the protecting group. The conversion of epoxyamides into epoxyalcohols was
- O?a, Noe,Romero-Carrasco, Antonio,Pino-González, M. Soledad
-
p. 156 - 163
(2013/04/10)
-
- Synthesis of a furanosyl-pyranone derivative related to the tri-o-heterocyclic core of herbicidins
-
A new compound that is structurally related to the undecose ring structure of herbicidins has been prepared. The synthesis of this novel furanosyl-pyranone derivative was made possible through the regioselective reductive ring-opening of a 3,5-O-benzylidene-D-xylofuranose and the hetero-Diels-Alder reaction of an aldehyde and a Danishefsky-type diene. The highly functionalized pyranone derivative can be a useful precursor for the synthesis of herbicidins.
- Hsu, Ching-Yun,Lee, I-Chi,Lico, Larry S.,Uang, Biing-Jiun,Hung, Shang-Cheng
-
experimental part
p. 421 - 425
(2012/08/08)
-
- Unexpected highly diastereoconvergent Grignard additions to d-xylofuranose-derived t-butanesulfinyl aldimines
-
Unexpected high levels of diastereoconvergence (dr >15:1) were observed in the addition of a series of Grignard reagents in THF to d-xylose-derived t-BS aldimines 2a,b affording (SS,5R)- and (RS,5R)-adducts. This anomaly was absent w
- Wang, Bing,Zhang, Pei-Pei
-
supporting information; experimental part
p. 119 - 122
(2012/01/17)
-
- Glycosynthase-Mediated Assembly of Xylanase Substrates and Inhibitors
-
An exo-β-xylosidase mutant with glycosynthase activity was created to aid in the synthesis of xylanase substrates and inhibitors. Simple monosaccharides were easily elaborated into di-, tri- and tetrasaccharides by using this enzyme. Some products proved
- Goddard-Borger, Ethan D.,Fiege, Brigitte,Kwan, Emily M.,Withers, Stephen G.
-
scheme or table
p. 1703 - 1711
(2012/06/29)
-
- SACCHARIDE STRUCTURES AND METHODS OF MAKING AND USING SUCH STRUCTURES
-
Described are oligosaccharides having a protecting group at two, a plurality, a majority of, or each position in the oligosaccharide which is amenable to derivatization. Collections, libraries and methods of making and using such oligosaccharides are also
- -
-
-
- SYNTHETIC ANALOGUES OF PHOSPHATIDYL-MYO-INOSITOL MANNOSIDES WITH AN INHIBITORY ACTIVITY OF THE INFLAMMATORY RESPONSE
-
The present invention relates to novel synthetic analogues of phosphatidyl-myo-inositol mannosides (hereinafter referred to as PIMs) of general formula (I): or a pharmaceutically acceptable salt thereof, to the method for preparing same and to the use thereof in the prevention or treatment of a disease associated with the overexpression of cytokines or of chemokines, in particular of TNF and/or of IL-12. The invention also relates to a pharmaceutical composition comprising at least one synthetic derivative of PIM.
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-
Page/Page column 15
(2011/10/04)
-
- A five-step formal synthesis of (-)-Jaspine B
-
A new application of the sequential hydrolysis-oxidation-Wittig olefination (SHOWO) protocol to a D-glu-cose derivative, and an anomeric deoxygenation reaction of a xylo-D-furanose derivative is presented for the five-step formal synthesis of (-)-Jaspine
- Cruz-Gregorio, Silvano,Espinoza-Rojas, Cristhian,Quintero, Leticia,Sartillo-Piscil, Fernando
-
experimental part
p. 6370 - 6371
(2011/12/22)
-
- First stereoselective total synthesis of stagonolide G
-
First stereoselective total synthesis of nonenolide stagonolide G involving a convergent strategy is described. The key reactions include Keck allylation and Grubbs ring closing metathesis reaction.
- Srihari,Kumaraswamy,Bhunia, Dinesh C.,Yadav
-
scheme or table
p. 2903 - 2905
(2010/06/14)
-
- Inverse stereoselectivity in the nucleophilic attack on five-membered ring oxocarbenium ions. Application to the total synthesis of 7-epi-(+)-goniofufurone
-
A highly stereoselective nucleophilic substitution at the anomeric position of 1,2-O-isopropylidene furanose derivatives was employed for the synthesis of 7-epi-(+)-goniofufurone and two of its stereoisomers. According to Woerpel's model, the stereoselect
- Hernández-García, Luís,Quintero, Leticia,H?pfl, Herbert,Sosa, Martha,Sartillo-Piscil, Fernando
-
experimental part
p. 139 - 144
(2009/04/07)
-
- Scalable synthesis of L-lduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides
-
L-ldo cyanohydrln 3 was prepared from dlacetone-D-glucose In four steps and 76% overall yield and 90% de via cyanohydrin reaction of aldehyde 2. This process can be scaled to provide >1 mol of pure L-Ido cyanohydrin 3. Cyanohydrin 3 was elaborated to 1,2-Isopropylldineprotected L-ldo nitrile (8), lduronic amide 9, and known carboxy ester 10. Coupling of 8 and 9 with glucosamine donors leads to new types (6-cyano and 6-carboxamlde) of heparin-related disaccharides.
- Hansen, Steen Uldall,Barath, Marek,Salameh, Bader A.B.,Pritchard, Robin G.,Stimpson, William T.,Gardiner, John M.,Jayson, Gordon C.
-
supporting information; experimental part
p. 4528 - 4531
(2009/12/09)
-
- Carbohydrate templates for the synthesis of prototype renin inhibitors
-
A concise synthesis of a prototype renin inhibitor and its 7-epimer has been accomplished starting from readily available d-glucose.
- Mohapatra, Debendra K.,Sahoo, Gokarneswar,Sankar, Kuppusamy,Gurjar, Mukund K.
-
scheme or table
p. 2123 - 2129
(2009/04/05)
-
- Design, synthesis and antiproliferative activity of two new heteroannelated (-)-muricatacin mimics
-
Two new (-)-muricatacin mimics bearing a furano-furanone ring and an oxygen isostere in the side chain have been designed and synthesized and their in vitro antiproliferative activity was evaluated against several human tumour cell lines. Both analogues showed an increased activity against HL-60 cells with 17- and 185-fold higher potency than (-)-muricatacin. A straightforward synthesis of (-)-muricatacin is also disclosed.
- Popsavin, Velimir,Sreco, Bojana,Benedekovic, Goran,Popsavin, Mirjana,Francuz, Jovana,Kojic, Vesna,Bogdanovic, Gordana
-
scheme or table
p. 5182 - 5185
(2009/05/07)
-
- Stereoselective synthesis of spiro-β-lactams using d-(+)-glucose derived chiral pool: remarkable influence of the torquoelectronic effect
-
Diastereoselective synthesis of spiro-β-lactams via [2+2] cycloaddition reaction of imines and chiral ketenes is described. The chiral ketene was prepared from commercially available, inexpensive d-glucose. Although, theoretically four diastereomers are p
- Chincholkar,Puranik, Vedavati G.,Deshmukh
-
p. 9179 - 9187
(2008/02/10)
-
- A new versatile strategy for C-aryl glycosides
-
(Chemical Equation Presented) A versatile strategy involving a sequential intermolecular enyne metathesis of C-alkynyl glycosides with ethylene, Diels-Alder, and aromatization reactions is successfully developed to provide a range of C-aryl glycosides.
- Kaliappan, Krishna P.,Subrahmanyam, Ayyagari V.
-
p. 1121 - 1124
(2007/10/03)
-
- Compounds that bind to the interferon-gamma, preparation method thereof and medicaments containing same
-
Compound capable of binding to gamma-interferon (γ-IFN), chosen from the molecules corresponding to formula (I) below: in which X is a divalent spacer group that is sufficiently long to allow the two oligosaccharide fragments A and B to each bind to one of the peptide sequences 125 to 143 of the C-terminal ends of a γ-interferon (γ-IFN) homodimer, n represents an integer from 0 to 10, and for example equal to 0, 1, 2, 3, 4 or 5, and each R independently represents a hydrogen atom, an SO3? group or a phosphate group, on the condition that no SO3? group is in the 3-position of the glucosamine units of compound (I). The invention also relates to the process for preparing these compounds, to the complexes formed by these compounds and gamma-interferon, and to the medicaments comprising these compounds or complexes.
- -
-
Page/Page column 21
(2008/06/13)
-
- PRODUCTION OF L-IDURONATE CONTAINING POLYSACCHARIDES
-
The present invention provides processes for the production of polysaccharides containing the L-iduronate subunit, for example, heparin-type polysaccharides. New intermediate compounds and processes developed during the production of said polysaccharides are also presented.
- -
-
Page/Page column 49
(2008/06/13)
-
- Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3′-C-ethynyluridine (EUrd) and 3′-C-ethynylcytidine (ECyd)
-
The synthesis of branched and conformationally restricted analogs of the anticancer nucleosides 3′-C-ethynyluridine (EUrd) and 3′-C- ethynylcytidine (ECyd) is presented. Molecular modeling and 1H NMR coupling constant analysis revealed that the furanose rings of all analogs except the LNA analog are conformationally biased towards South conformation, and are thus mimicking the structure of ECyd. All target nucleosides were devoid of anti-HIV or anticancer activity.
- Hrdlicka, Patrick J.,Andersen, Nicolai K.,Jepsen, Jan S.,Hansen, Flemming G.,Haselmann, Kim F.,Nielsen, Claus,Wengel, Jesper
-
p. 2597 - 2621
(2007/10/03)
-
- [3+2] Cycloaddition reactions: A simple entry to the 1-aza-2-oxo-3,4,5,6- tetrahydroxybicyclo[3.3.0]octane ring system
-
The [3+2] intramolecular nitrone cycloaddition (INC) reaction on appropriately designed olefinic nitrones derived from D-glucose, having the nitrone at C-1 and α,β-unsaturated ester functionalities at C-5 of the sugar backbone, afforded the isoxazolidine
- Roy, Ashim,Roy, Biswajit G.,Achari, Basudeb,Mandal, Sukhendu B.
-
p. 5811 - 5814
(2007/10/03)
-
- Synthesis of iduronic acid building blocks for the modular assembly of glycosaminoglycans
-
The modular synthesis of glycosaminoglycans requires straightforward methods for the production of large quantities of protected uronic acid building blocks. In particular, the preparation of fully differentiated iduronic acids has proven particularly cha
- Lohman, Gregory J. S.,Hunt, Diana K.,H?germeier, Jens A.,Seeberger, Peter H.
-
p. 7559 - 7561
(2007/10/03)
-
- Efficient preparation of three building blocks for the synthesis of heparan sulfate fragments: Towards the combinatorial synthesis of oligosaccharides from hypervariable regions
-
New, multigram routes to suitably protected L-iduronyl monosaccharide donors 4 and 5 and 2-azidoglucose acceptors 6 and 7 are described. The L-iduronyl and D-glucuronyl disaccharides 1-3 were then prepared from these compounds, by means of efficient and regioselective protective group manipulations. These disaccharides form the basis of a combinatorial approach toward the synthesis of heparan sulfate fragments representative of the heterogeneous regions of this polysaccharide. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)Introduction.
- Gavard, Ollivier,Hersant, Yael,Alais, Jocelyne,Duverger, Veronique,Dilhas, Anna,Bascou, Alison,Bonnaffe, David
-
p. 3603 - 3620
(2007/10/03)
-
- Introduction of a carbohydrate moiety into the structure of thiourea compounds targeting HIV-1 reverse transcriptase
-
We developed a novel approach to introduce a carbohydrate moiety into the structure of thiourea compounds targeting the NNI binding pocket of the HIV-1 reverse transcriptase. The described method involves the synthesis of an amino-substituted carbohydrate moiety which is then condensed with various thiocarbonylimidazole derivatives of substituted aromatic amines.
- Goud, P. Mallikarjun,Venkatachalam,Uckun
-
p. 1185 - 1193
(2007/10/03)
-
- Asymmetric synthesis of azetidin-2-ones by [2+2] cycloaddition using chiral imines derived from D-(+)-glucose
-
Asymmetric synthesis of β-lactams by the [2+2] cycloaddition of ketenes with chiral imines derived from D-(+)-glucose was carried out; predominantly cis-β-lactams were formed with very high diastereoselectivity. The stereochemistry at C-3 and C-4 was esta
- Arun,Joshi,Puranik,Bhawal,Deshmukh
-
p. 2309 - 2316
(2007/10/03)
-
- Synthesis of L-α-phosphatidyl-D-myo-inositol 3,5-bisphosphate from D-glucose
-
Efficient synthesis of L-α-phosphatidyl-D-myo-inositol 3,5-bisphosphate was achieved from 1,2,5,6-diisopropylidene-D-glucose by utilizing ring-closing metathesis and catalytic OsO4 dihydroxylation.
- Nishikawa, Asuka,Saito, Shintaro,Hashimoto, Yuichi,Koga, Kenji,Shirai, Ryuichi
-
p. 9195 - 9198
(2007/10/03)
-
- Study of stereoselectivity in organometallic additions to 1,2-O-isopropylidene-O-R-α-D-xylopentodialdo-1,4-furanose
-
Diastereofacial selectivity of the addition of organometallic reagents to 1,2-O-isopropylidene-O-R-α-D-xylopentodialdo-44-furanose (6) was studied.
- Gracza, Tibor,Szolcsanyi, Peter
-
p. 1386 - 1398
(2007/10/03)
-
- Elongation of the pentose chain at the terminal carbon atom with Grignard C1 reagents. A study of the homologation reaction
-
Derivatives of four stereoisomeric pentodialdo-1,4-furanoses were reacted with four Grignard C1 reagents: methoxymethyl-, allyloxymethyl-, benzyloxymethyl, and dimethylphenylsilylmethyl-magnesium chlorides. Derivatives of the expected stereoisomeric hexoses were accompanied in some cases by C-4 inverted products. The results have been discussed in terms of α- and β-chelated transition states. It has been found that the RX (X=O,Si) grouping of the Grignard reagent strongly influences the stereochemical outcome of the elongation reaction.
- Stepowska, Halszka,Zamojski, Aleksander
-
p. 5519 - 5538
(2007/10/03)
-
- An epoxide derived from D-glucose as the key intermediate for penaresidine and sphingolipids synthesis
-
A multigram-scale synthesis of 3R,4R,5R 3,5-dibenzyloxy-4-p- methoxybenzyl-1,2-epoxypentane and its use as intermediate for sphingolipids, penazeridine and penazetidine synthesis are described.
- Beauhaire, Josiane,Ducrot, Paul-Henri
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p. 2443 - 2456
(2007/10/03)
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- The reaction of (methylthio)acetyliron complex with pentose terminal aldehydes
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The reaction between anion generated from (methylthio)acetyliron complex (1) and four stereoisomeric dialdo-1,4-furanoses was performed. Each aldehyde led to mixtures (6-8) of stereoisomeric aldols. Aldols were separated and their configuration was determ
- Wisniewski,Zamojski
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p. 1937 - 1948
(2007/10/03)
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- Synthesis of unnatural enantiomer of nectrisine and its biological activity
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ent-Nectrisine (2), the unnatural enantiomer of nectrisine (1), a potent α-glucosidase inhibitor, was synthesized from D-glucose derivative. Biological assay showed that 2 had no significant bioactivity.
- Kogoshi, Naoto,Takatsuki, Akira,Kim, Yong Jip,Kitahara, Takeshi
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- Synthetic study on chiral building block of vicinal diol, chiron approach to the precursors of all sphingosine stereoisomers
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All enantiomeric stereoisomers of 1,2,3-trihydroxy-4E-octadecene, key intermediates for the syntheses of sphingosines, were prepared using sugar as chiral pool.
- Li, Yun-Long,Sun, Xiao-Ling,Wu, Yu-Lin
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p. 10727 - 10738
(2007/10/02)
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- Michael addition of malononitrile to chiral α-acylacrylates
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Starting from 2,3-O-isopropylidene-D-glyceraldehyde (1), 3-O-methyl and 3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose (4a, 4b), we describe the synthesis of the α-acyl-β-alkyl substituted acrylates 2 and 5. The Michael addition of malononitrile to these substrates gives the polyfunctionalized 2-amino-4H-pyrans 3 and 6 with moderate diastereoselectivity and reasonable overall yield from diols 7 and 8a,b. A detailed analysis is performed scanning different type of bases in the Michael reaction. We find that, while for acceptor 2 no changes are observed, for compound 5 the stereochemical outcome of the 1,4-addition is reversed in going from piperidine, sodium hydride or potassium t-butoxide to lithium diisopropylamide or lithium diisopropylamide/magnesium iodide reagent. Several models fro rationalising the results are proposed.
- Marco, Jose L.,Martin, Gemma,Martin, Nazario,Martinez-Grau, Angeles,Seoane, Carlos,Albert, Armando,Cano, Felix H.
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p. 7133 - 7144
(2007/10/02)
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- Stereoselective Synthesis of Unnatural Stereoisomers of LL-P880β and LL-P880γ, Pestatolin Analogues from Penicillium sp.
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A synthesis of unnatural stereoisomers of LL-P880β and (2) and subsequent transformation of 2 into LL-P880γ (3) were achieved by starting from diacetoneglucose (4).A chiral building block, 5-deoxy-α-D-ribofuranose derivative 9, was derived from 4 by two s
- Kirihata, Mitsunori,Ohe, Masayuki,Ichimoto, Itsuo,Ueda, Hiroo
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p. 1825 - 1828
(2007/10/02)
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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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