cas 22529-61-9, 1,2-O-ISOPROPYLIDENE-3-BENZYLOXY-D-GLUCOFURANOSE

Articles about 22529-61-9Total 88 be found

Article title
Article abstract
Author
Journal number and time
Download

A Glucose-Derived α-Hydroxy Aldehyde for the Petasis Reaction: Facile Access to Polyfunctional δ-Amino Acids
The multicomponent Petasis borono-Mannich reaction proceeds via an imine with the boronic acid acting as the nucleophile for the preparation of amines and their derivatives, including amino acids. In view of the expansion of the poorly-exploited carbohydr
Lenci, Elena,Bellini Puglielli, Raffaele,Bucaletti, Elisabetta,Innocenti, Riccardo,Trabocchi, Andrea
p. 4227 - 4234
(2020)
Read Online

Synthesis and antimicrobial activity of (?)-cleistenolide and analogues
Using the “chiral pool” approach, two modified total syntheses of the biologically active δ-lactone cleistenolide (1) have been achieved starting from D-glucose. These approaches also enabled the preparation of novel analogues and derivatives of natural product 1. The applied strategy for the synthesis of 1 involves: the initial degradation of the chiral precursor for a single C-atom, C2-fragment chain extension using Z-selective Wittig reaction, and the final δ-lactonization. All tested cleistenolide analogues displayed antimicrobial activity against a panel of nine microbial strains, most of them superseding the activity of cleistenolide itself, and, in some cases, coming close in value to the observed minimal inhibitory concentrations of chloramphenicol. Increased lipophilicity of the derivatives and the non-sterically congested conjugated lactone moiety were a prerequisite for analogues with high inhibitory activity against S. aureus and, in general, Gram-positive bacteria.
Benedekovi?, Goran,Popsavin, Mirjana,Radulovi?, Niko S.,Stojanovi?-Radi?, Zorica,Farkas, Sándor,Francuz, Jovana,Popsavin, Velimir
(2020/12/07)

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
(2020/07/24)

Synthesis of glycosylated aminothiol from D-glucose as promising anti-tubercular agent
A facile method for a series of novel glycosylated β-aminothiols by employing TBAB/NEt3-catalyzed ring opening of thiirane ring of D-glucose-derived 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose with different primary and secondary amines including aliphatic, aromatic, heterocyclic, and glycosyl amine has been devised. Diamines on the other hand for thiirane ring opening of anhydroglucose derivative led to the formation of respective bis-glycosylated N1,Nn-diaminothiols in good yield. The method is straight forward, economical, high-yielding and easy to scale up. One of the glycosylated aminothiol contains both the hydrophilic carbohydrate moiety and hydrophobic hexadecyl residue, thus can serve a promising candidate to exhibit surface-active properties. The resulted glycosylated β-aminothiols may serve as an interesting scaffold to develop mechanism-based novel chemotherapeutic agents.
Singh, Archana,Prasad, Virendra,Rajkhowa, Sanchayita,Tripathi, Vishwa D.,Tiwari, Vinod K.
p. 213 - 225
(2020/03/18)

Gram-level total synthesis method of sulfur onium salt type natural product neoponkoranol extracted from salacia plants
The invention belongs to the field of chemical synthesis and particularly relates to a gram-level total synthesis method of a sulfur onium salt type natural product neoponkoranol with hypoglycemic activity extracted from salacia plants. According to the m
-
Paragraph 0033; 0034; 0035; 0036

(2019/02/19)

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)

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 0055; 0076-0078

(2018/04/21)

Syntheses and complexing ability of α-d-gluco- and α-d-xylofuranoside-based lariat ethers
Chiral monoaza-15-crown-5 lariat ethers attached to a 1,2-O-isopropylidene-α-d-glucofuranoside unit (10–13), monoaza-16-crown-5 lariat ethers fused to 1,2-O-isopropylidene-α-d-glucofuranoside- (18) and to 1,2-O-isopropylidene-α-d-xylofuranoside units (23 and 24) have been synthesized. The alkali metal- and ammonium picrate extracting ability of these macrocycles was investigated in dichloromethane–water system. In general, the 15-membered macrocycles (10–13) showed, for almost all cations, a more considerable extracting ability, than the 16-membered lariat ethers (18, 23 and 24). Plasticized PVC membrane electrodes (ISEs) were prepared from the α-d-glucofuranoside-based triphenylmetyl (trityl) ether derivative (18), and its potentiometric selectivities and complex formation constants were determined with the segmented sandwich membrane method. Furthermore, the binding affinities of ionophores to different metal ions were also measured by competitive ESI–MS experiments. One of the 1,2-O-isopropylidene-α-d-glucofuranoside-based lariat ethers (13) exhibited a high selectivity for silver ion (Ag+).
Rapi, Zsolt,Ozohanics, Oliver,Tóth, Gábor,Bakó, Péter,H?fler, Lajos,Nemcsok, Tamás,Kánya, Nándor,Keglevich, Gy?rgy
p. 19 - 32
(2016/05/19)

A stereoselective approach for the total synthesis of (-)-tadanalactam from acetonide-d-glucose
A stereoselective and realistic approach for the total synthesis of naturally occurring δ-lactam (-)-tadanalactam, has been accomplished from the commercially existing acetonide-d-glucose involving Birch reduction, Pinnick oxidation, Staudinger reaction,
Konda, Saidulu,Kurva, Bhaskar,Nagarapu, Lingaiah,Dattatray, Akkewar M.
p. 834 - 836
(2015/03/03)

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)

METHOD FOR PREPARING 3-O-BENZYL-1,2-O-ISOPROPYLIDENE-A-L-FURAN IDOSE
Provided is a method for preparing 3-O-benzyl-1,2-O-isopropylidene-α-L-idofuranose, which comprises: (1) protecting hydroxyl of 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (III) by benzoyl and methylsulfonyl to obtain 6-O-benzoyl-3-O-benzyl-1,2-O-is
-
Paragraph 0026-0028

(2015/03/16)

Structure-activity relationships of β-hydroxyphosphonate nucleoside analogues as cytosolic 5′-nucleotidase II potential inhibitors: Synthesis, in vitro evaluation and molecular modeling studies
The cytosolic 5′-nucleotidase II (cN-II) has been proposed as an attractive molecular target for the development of novel drugs circumventing resistance to cytotoxic nucleoside analogues currently used for treating leukemia and other malignant hemopathies
Meurillon, Ma?a,Marton, Zsuzsanna,Hospital, Audrey,Jordheim, Lars Petter,Béjaud, Jér?me,Lionne, Corinne,Dumontet, Charles,Périgaud, Christian,Chaloin, Laurent,Peyrottes, Suzanne
p. 18 - 37
(2014/03/21)

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)

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)

METHOD FOR PREPARING 3-O-BENZYL-1,2-O-ISOPROPYLIDENE- -L-FURAN IDOSE
Provided is a method for preparing 3-O-benzyl-1,2-O-isopropylidene-α-L-idofuranose, which comprises: (1) protecting hydroxyl of 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (III) by benzoyl and methylsulfonyl to obtain 6-O-benzoyl-3-O-benzyl-1,2-O-is
-
Paragraph 0020

(2015/01/18)

Ultrasound-assisted selective deprotection of terminal acetonides catalyzed by silica-supported boron trifluoride
An efficient and convenient method for the selective cleavage of terminal acetonides is described. Treatment of terminal acetonides in the presence of a wide range of functional groups with silica-supported boron trifluoride as a catalyst furnished the corresponding diols in 82-95% yield under ultrasound irradiation conditions. The acid-labile p-methoxybenzyl group as a protecting group remained intact under the conditions employed to the present deprotection condition. Copyright Taylor & Francis Group, LLC.
Xiong, Junlong,Yan, Shiqiang,Ding, Ning,Zhang, Wei,Li, Yingxia
p. 184 - 192
(2013/07/27)

N-Thiocarbonyl iminosugars: Synthesis and evaluation of castanospermine analogues bearing oxazole-2(3H)-thione moieties
A straightforward and efficient synthetic route to a new class of glycosidase inhibitors containing an oxazole-2(3H)-thione moiety has been devised. The approach involves the formation of α-hydroxy ketones, which, after condensation with thiocyanic acid, leads to the formation of the heterocycle. By exploiting the ability of the nitrogen atom of oxazoline-2-thione precursors to act as nucleophiles in intramolecular addition, castanospermine analogues could be readily prepared in good overall yields. Glycosidase inhibitory activity compared to oxazolidinethione analogues showed a strong influence of the double bond, for example with pseudoiminosugar 19, by suppressing α-glucosidase inhibition and introducing, to a moderate level, β-glucosidase inhibitory activity. Reactivities showed the propensity of oxazole-2(3H)-thiones - especially when fused on carbohydrate frames - to convert into 1,3-oxazolidine-2-thione aminals through nucleophilic addition to the double bond, leading to unexpected tricyclic structure 21. Oxazole-2(3H)-thione moieties have been anchored onto carbohydrates in a five-step sequence that allows access to castanospermine analogues. Copyright
Silva, Sandrina,Sanchez-Fernandez, Elena M.,Ortiz Mellet, Carmen,Tatibouet, Arnaud,Pilar Rauter, Amelia,Rollin, Patrick
p. 7941 - 7951
(2014/01/06)

PROCESS FOR PREPARING HEPARINOIDS AND INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF
Processes are disclosed for the synthesis of the Factor Xa anticoagulant fondaparinux and related compounds. Protected pentasaccharide intermediates and efficient and scalable processes for the industrial scale production of fondaparinux sodium by conversion of the protected pentasaccharide intermediates via a sequence of deprotection and sulfonation reactions are provided.
-
Page/Page column 13

(2013/02/28)

PROCESS FOR PREPARATION OF FONDAPARINUX AND ITS INTERMEDIATES
The present invention relates to a process for the preparation of 3-O-benzyl- 1,2-O- isopropylidene-α-D-glucofuranuronic acid (Formula IV) and ester (Formula V) thereof. The process comprises benzylation of l,2:5,6-di-O-isopropylidene-α-D-glucofuranose (Formula I; hereinafter, referred to as diacetone-D-glucose) in the presence of tetrabutylammonium bromide, followed by selective hydrolysis of the product formed (Formula II) using sulfuric acid to obtain 3-O-benzyl- 1,2-O-isopropylidene-α-D- glucofuranose (Formula III). Compound of Formula III is then oxidized to compound of Formula IV which upon esterification provides corresponding ester of Formula V. The process of the invention can be used in the production of fondaparinux sodium, a heparin and blood clotting factor Xa inhibitor.(Formula I, II, III, IV, V) (I) (II) (III) (IV) (V) wherein R is optionally branched alkyl group.
-
Page/Page column 22

(2013/03/26)

METHODS AND INTERMEDIATES FOR THE PREPARATION OF FONDAPARINUX
The present invention relates to methods for the synthesis of fondaparinux and intermediates thereto.
-
Paragraph 00196; 00197

(2014/01/08)

Environment friendly chemoselective deprotection of acetonides and cleavage of acetals and ketals in aqueous medium without using any catalyst or organic solvent
Highly chemoselective environment friendly deprotection of acetonides and cleavage of acetals and ketones has been achieved by heating in aqueous medium without using any catalyst and organic solvent. Indian Academy of Sciences.
Mukherjee,Sengupta,Roy
p. 1493 - 1496
(2014/04/03)

Disaccharide-containing macrocycles by click chemistry and intramolecular glycosylation
In this study o- and m-xylylene moieties in combination with a triazolylmethyl moiety have been successfully employed as a relatively rigid spacer system in intramolecular glycosylation reactions. Phenyl 3,4,6-tri-O-benzyl-2-O-propargyl-1-thio-D-glucopyra
Tiwari, Vinod K.,Kumar, Amit,Schmidt, Richard R.
supporting information; experimental part
p. 2945 - 2956
(2012/07/27)

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)

Intramolecular base-free sonogashira reaction for the synthesis of benzannulated chiral macrocycles embedded in carbohydrate templates
A base-free, intramolecular Sonogashira reaction-based general approach has been established for the diversity-oriented synthesis (DOS) of fused bi- and tricyclic systems containing benzannulated, 10- to 13-membered chiral macrocycles embedded in carbohydrate templates. Macrocycles with different ring sizes have been prepared by pre-designing the chiral building blocks. Base-sensitive groups like acetyl and TBDPS survived the reaction conditions. Copyright
Hussain, Altaf,Yousuf, Syed Khalid,Kumar, Deepak,Lambu, Malikharjunarao,Singh, Baldev,Maity, Sudip,Mukherjee, Debaraj
supporting information; experimental part
p. 1933 - 1940
(2012/09/22)

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
-
Page/Page column 22

(2011/09/14)

Chemoenzymatic synthesis of C8-modified sialic acids and related α2-3- and α2-6-linked sialosides
Naturally occurring 8-O-methylated sialic acids, including 8-O-methyl-N-acetylneuraminic acid and 8-O-methyl-N-glycolylneuraminic acid, along with 8-O-methyl-2-keto-3-deoxy-d-glycero-d-galacto-nonulosonic acid (Kdn8Me) and 8-deoxy-Kdn were synthesized fro
Yu, Hai,Cao, Hongzhi,Tiwari, Vinod Kumar,Li, Yanhong,Chen, Xi
scheme or table
p. 5037 - 5040
(2011/10/09)

Useful methods for the synthesis of isopropylidenes and their chemoselective cleavage
A catalytic amount of phosphotungstic acid (PTA) has been found to be a very effective catalyst for isopropylidenation of 1,2-diols and their deprotection at room temperature. The ease of handling, cost and activity of the catalyst, good to excellent yields and chemoselectivity for deprotection are some of the highlights of the reported method.
Vanlaldinpuia, Khiangte,Bez, Ghanashyam
supporting information; experimental part
p. 3759 - 3764
(2011/08/06)

Novel formal synthesis of stereospecifically C-6 deuterated d-glucose employing configurationally stable alkoxymethyllithiums
The synthesis and testing of configurational stability of chirally monodeuterated PMB- and THP-substituted oxymethyllithiums are described. Macroscopically they are configurationally stable up to -35 °C, the limit of their chemical stability, and microscopically even up to 0 °C. Furthermore, THP-protected oxy-[D1]methyllithium has been applied in the formal synthesis of (6R)-[6-D1]-d-glucose (four steps, 40% yield), an example of its use as a homochiral hydroxymethyl synthon.
Kapeller, Dagmar C.,Hammerschmidt, Friedrich
experimental part
p. 591 - 598
(2010/09/05)

Mild, versatile, and chemoselective indium(III) triflate-catalyzed deprotection of acetonides under microwave heating conditions
A series of acetonides (both terminal and internal isopropylidene acetals) have been deprotected under catalytic, neutral conditions to give their corresponding 1,2-diols. The reactions utilize indium(III) triflate in the presence of water and an organic solvent with mild microwave heating. Terminal acetonides are chemoselectivley removed in the presence of internal acetonides; acid labile functional groups remain intact under these conditions, thereby greatly enhancing the scope of the reaction substrates that can be utilized with this approach.
Golden, Kathryn C.,Gregg, Brian T.,Quinn, John F.
experimental part
p. 4010 - 4013
(2010/08/07)

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)

Unambiguous syntheses of 3-o-benzyl-1,5-dideoxy-1,5-imino-d-glucitol and-l-iditol
Short and unambiguous syntheses of 3-O-benzyl-1,5-dideoxy-1,5-imino-d- glucitol and -l-iditol are described. The compound previously reported as 3-O-benzyl-1,5-dideoxy-1,5-imino-d-glucitol (Roy, A.; Achari, B.; Mandal, S. B. Synthesis 2006, 1035) is shown to be actually 3-O-benzyl-1,5-dideoxy-1,5-imino- l-iditol. Georg Thieme Verlag Stuttgart New York.
Csiki, Zsuzsanna,Fuegedi, Peter
experimental part
p. 2626 - 2630
(2010/09/11)

Synthesis of highly functionalized amino acids: An expedient access to L- and D-β-hydroxyenduracididine derivatives
The nonproteinogenic amino acids (3S,4S)-L- and (3S,4S)-Dβ- hydroxyenduracididine (βhEnd), each containing a cyclic guanidine group and three contiguous stereocenters, have been synthesized for the first time, starting from commercially available diaceton
Schwoerer, Clemens J.,Oberthuer, Markus
supporting information; experimental part
p. 6129 - 6139
(2010/03/24)

Zeolite catalyzed selective deprotection of di- and tri-O-isopropylidene sugar acetals
H-Beta zeolite, a microporous solid acid, is demonstrated to be an efficient catalyst for the selective deprotection of cyclic as well as acyclic O-isopropylidene sugar acetals derived from d-glucose, d-xylose, d-mannose, and d-mannitol in aqueous MeOH at room temperature. A notable observation is the conversion of d-mannitol triacetonide into 1,2:3,4-di-O-isopropylidene-d-mannitol (48%) and 3,4-O-isopropylidene-d-mannitol (36%) brought about in 6 h by H-beta zeolite and the non-occurrence of any hydrolysis in the case of H-ZSM-5 catalyzed reaction in 24 h under the same conditions.
Bhaskar, Pallooru Muni,Mathiselvam, Manoharan,Loganathan, Duraikkannu
p. 1801 - 1807
(2008/12/21)

Truly catalytic and chemoselective cleavage of benzylidene acetal with phosphomolybdic acid supported on silica gel
Phosphomolybdic acid supported on silica gel provides a truly catalytic method for the chemoselective cleavage of benzylidene acetals having sensitive functional groups under mild conditions. It is easy to perform on large scale owing to minimal catalyst loading (0.5 mol-%). Several sensitive functional groups such as TBDPS ether, -OMs, -OAc, allyl ether, N-Boc, N-Fmoc and N-Cbz are stable under the reaction conditions. In addition, benzylidene acetal is selectively cleaved in the presence of isopropylidene ketal. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Kumar, Ponminor Senthil,Kumar, Gaddale Devanna Kishore,Baskaran, Sundarababu
supporting information; scheme or table
p. 6063 - 6067
(2009/05/27)

Ce(IV) ammonium nitrate catalyzed chemoselective deprotection of acetonides
Highly chemoselective deprotection of diacetone sugars have been achieved at room temperature in excellent yields using commercially available eerie ammonium nitrate (20 mol%) in moist CH3CN.
Jana,Roy
p. 707 - 709
(2008/09/18)

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)

Sulfuric acid immobilized on silica: an efficient reusable catalyst for selective hydrolysis of the terminal O-isopropylidene group of sugar derivatives
Sulfuric acid immobilized on silica proved to be an efficient catalyst for selective hydrolysis of the terminal O-isopropylidene group of sugar derivatives. The method is very simple and economic for large-scale synthesis in which the catalyst is recovered and reused for several runs. Reactions with di-O-isopropylidene derivatives of d-glucose, d-mannose, d-fructose and l-sorbose led to the formation of the corresponding mono-O-isopropylidene derivatives in good to excellent yields.
Rajput, Vishal Kumar,Roy, Bimalendu,Mukhopadhyay, Balaram
p. 6987 - 6991
(2007/10/03)

A short and simple synthesis of 1-deoxynojirimycin derivatives from D-glucose
Insertion of an amino functionality at C-5 of D-glucose with inversion of configuration, followed by imine formation with the latent aldehyde at C-1 and concomitant reduction furnished the 1-deoxynojirimycin skeleton. Georg Thieme Verlag Stuttgart.
Roy, Ashim,Achari, Basudeb,Mandal, Sukhendu B.
p. 1035 - 1039
(2007/10/03)

Nonfluorous, highly CO2-soluble chelating ligands for scCO 2 metal ion extraction
A series of new nonfluorous chelating ligands derived from glucose have been designed and synthesized. All compounds are highly soluble in liquid or supercritical carbon dioxide. Solubility trend of these chelating compounds would be rationalized by the i
Yang, Hai-Jian
p. 1000 - 1001
(2007/10/03)

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 48

(2008/06/13)

Catalytic asymmetric dihydroxylation of olefins using polysulfone-based novel microencapsulated osmium tetroxide
A polysulfone based novel polymer-supported osmium catalyst has been developed. The catalyst was prepared from commercially available polysulfone, based on a microencapsulation technique and was employed in the asymmetric dihydroxylation of various olefins using (DHQD)2PHAL as the chiral ligand and NMO as the co-oxidant in H2O-acetone-CH3CN (1:1:1). The catalyst was recovered by simple filtration and was reused to obtain excellent yields with good enantioselectivity up to five times.
Malla Reddy,Srinivasulu,Venkat Reddy,Narasimhulu,Venkateswarlu
p. 5285 - 5288
(2007/10/03)

Phosphomolybdic acid supported on silica gel: An efficient, mild and reusable catalyst for the chemoselective hydrolysis of acetonides
Carbohydrate acetonides were chemoselectively cleaved to the corresponding diols by using environmentally benign phosphomolybdic acid (H 3PMo12O40) supported on silica gel (PMA-SiO2) at ambient temperature in a
Yadav,Raghavendra,Satyanarayana,Balanarsaiah
p. 2461 - 2464
(2007/10/03)

Chemoselective hydrolysis of terminal isopropylidene acetals in acetonitrile using molecular iodine as a mild and efficient catalyst
A simple, mild and efficient method for deprotection of acetonides in the presence of molecular iodine is described. Acid labile protecting groups such as PMB, OMe, OBn, allyl and propargyl are compatible with the reaction conditions, while TBS, TBDPS, TMS and THP ethers were unstable under the same conditions.
Yadav,Satyanarayana,Raghavendra,Balanarsaiah
p. 8745 - 8748
(2007/10/03)

Selective deprotection of terminal isopropylidene acetals and trityl ethers using HClO4 supported on silica gel
Terminal isopropylidene acetals are selectively cleaved to the corresponding 1,2-diols in good to excellent yields in 6-24 h at room temperature by using the 'HClO4?SiO2' reagent system. Likewise, trityl ethers are readily cleaved to the corresponding alcohols in good to excellent yields within 2-3 h at room temperature. Work-up involves merely filtration of the reagent followed by purification of the crude product.
Agarwal, Aditi,Vankar, Yashwant D.
p. 1661 - 1667
(2007/10/03)

Polymer-supported ferric chloride as a heterogeneous catalyst for chemoselective deprotection of acetonides
Acetonides undergo chemoselective deprotection to afford the corresponding 1,2-diols in excellent yields using polymer (PVP)-supported ferric chloride as a heterogeneous catalyst in acetonitrile-dichloromethane at room temperature.
Chari, M. Adharvana,Syamasundar
p. 708 - 710
(2007/10/03)

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)

Chemoselective deprotection of acid labile primary hydroxyl protecting groups under CBr4-photoirradiation conditions
The CBr4-photoirradiation in methanol generates a controlled source of HBr, which can chemoselectively deprotect commonly used hydroxyl-protecting groups in saccharides and nucleosides, such as tert-butyldimethylsilyl, isopropylidene, benzylidene and triphenyl ethers in the presence of other acid-labile functional groups. Graphical Abstract.
Chen, Ming-Yi,Patkar, Laxmikant N.,Lu, Kuo-Cheng,Lee, Adam Shih-Yuan,Lin, Chun-Cheng
p. 11465 - 11475
(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 a polysulfated heparin degradation product
Two suitable methods for the synthesis of the heparin degradation product 2,5-anyhydro-3-O-(α-L-ido-pyranosyluronate)-D-mannitol hexa O-sulfate are reported. The synthesis pathways start from D-glucose and D-glucosamine.
Kuszmann, Janusz,Medgyes,Boros
p. 344 - 348
(2007/10/03)