- Regio- And diastereoselective Pd-catalyzed synthesis of C2-aryl glycosides
-
An efficient regio- and diastereoselective arylation method of readily available 2,3-glycals with various aryl iodides has been established. Using the Pd(OAc)2/AsPh3 precatalytic system, this protocol proved to be general to prepare a variety of substituted C2-aryl glycosides in good yields with complete diastereoselectivity.
- Alami, Mouad,Franco, Rémi,Gandon, Vincent,Ghouilem, Juba,Messaoudi, Samir,Retailleau, Pascal
-
supporting information
p. 7175 - 7178
(2020/07/14)
-
- Selective Synthesis of Some Aminosugars via Catalytic Aminohydroxylation of Protected 2,3-Unsaturated d -Gluco- And d -Galacto-2-hexenopyranosides
-
The aminohydroxylation of methyl 4,6-di-O-(tert-butyldimethylsilyl)-2,3-unsaturated α-d-glucopyranoside proceeds in the presence of chloramine-T, OsO4 (4 mol %), (DHQ)2PHAL (5 mol %), and triethylbenzylammonium chloride (TEBAC) in both a stereoselective a
- Fukuhara, Ippei,Matsubara, Ryosuke,Hayashi, Masahiko
-
supporting information
p. 9179 - 9189
(2020/08/14)
-
- Montmorillonite-catalyzed glysosylation of alcohols with glycals derived from galactose and glucose under microwave-induced reactions
-
Montmorillonite K10-catalyzed glycosylation of alcohols with glycals obtained from galactose and glucose is performed efficiently using microwave irradiation with good anomeric selectivity.
- Yadav, Ram Naresh,Banik, Indrani,Banik, Bimal Krishna
-
p. 1385 - 1387
(2020/06/27)
-
- Selective Synthesis of Partially Protected d -Talopyranosides and d -Gulopyranosides via Catalytic Asymmetric Dihydroxylation: Multiplier Effects of Substrate Control and Catalyst Control
-
Highly selective syntheses of d-talopyranosides and d-gulopyranosides have been achieved by utilizing the multiplier effects of substrate control and catalyst control. Through the combination of an O-benzoyl-protected substrate and the AD-mix-β system, the d-talopyranoside was obtained in a ratio of 96:4. In contrast, the d-gulopyranoside was obtained in a ratio of 3:97 through the use of an O-tert-butyldimethylsilyl-protected substrate and AD-mix-α.
- Namito, Yoichi,Michigami, Kyosuke,Nagahashi, Takaaki,Matsubara, Ryosuke,Hayashi, Masahiko
-
supporting information
p. 6058 - 6061
(2016/12/09)
-
- Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)-C(3) Unsaturated and α-d-Mannopyranosyl Sulfones
-
An efficient and divergent approach to C(2)-C(3) unsaturated glycosyl and α-d-mannopyranosyl sulfones has been developed via ruthenium-promoted direct glycosylation, oxidation, and dihydroxylation from glycal in one-pot. The presence of stoichiometric amounts of NaIO4 and in situ generation of RuO4 from a RuCl3-NaIO4 reagent system were crucial for chemoselective oxidation of sulfide in the presence of an olefin moiety. The dual-role of ruthenium in sequential glycosylation-oxidation-dihydroxylation is amenable to a wide range of thio acceptors to access α-d-mannopyranosyl sulfones in good yields with high regioselectivity.
- Chittela, Sravanthi,Reddy, Thurpu Raghavender,Radha Krishna, Palakodety,Kashyap, Sudhir
-
p. 7108 - 7116
(2015/07/28)
-
- Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI2-mediated cyclization
-
A convergent synthesis of the ABC ring of antitumor natural product paclitaxel (Taxol) is described. SmI2-mediated reductive cyclization of an allylic benzoate possessing an aldehyde function, synthesized from tri-O-acetyl-d-glucal and 1,3-cyclohexanedione, smoothly afforded the highly strained 6-8-6 tricarbocyclic structure in 66% yield.
- Fukaya, Keisuke,Tanaka, Yuta,Sato, Ayako C.,Kodama, Keisuke,Yamazaki, Hirohisa,Ishimoto, Takeru,Nozaki, Yasuyoshi,Iwaki, Yuki M.,Yuki, Yohei,Umei, Kentaro,Sugai, Tomoya,Yamaguchi, Yu,Watanabe, Ami,Oishi, Takeshi,Sato, Takaaki,Chida, Noritaka
-
supporting information
p. 2570 - 2573
(2015/06/16)
-
- Linearization of carbohydrate derived polycyclic frameworks
-
We report easy access to carbohydrate derived diverse tricyclic skeletons which could be beneficial for exploring polyfunctionalized chiral alicycles. The key reaction to assemble a sugar fused tricyclic core is intermolecular tandem esterification and 1,3-dipolar cycloaddition. The framework was elaborated using amide forming reactions, opening of isoxazolidine rings followed by N and O-acylations. The sequences provide distinct, spatially separated and encoded chemical entities that may pave the way to investigate cell functions.
- Singh, Priyanka,Panda, Gautam
-
p. 31892 - 31903
(2014/08/18)
-
- Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions
-
Catalytic amounts of tellurium(IV) tetrachloride were used to promote the O-glycosylation of 3,4,6-tri-O-acetyl-d-glucal to give the corresponding 2,3-unsaturated-O-glycosides. With simple alcohols, the desired compounds were obtained in good yields and excellent anomeric selectivity in a short reaction time using only 2 mol % of the catalyst. The application of the method in the synthesis of a small set of glycopyranosides with rigid or flexible linkers gave the corresponding α anomers as products in good yields. Further applications of some of the synthesized compounds in allylation reaction of aldehydes gave the corresponding homoallylic alcohols in good yields.
- Freitas, Juliano C. R.,Couto, Tulio R.,Paulino, Antonio A. S.,Malvestiti, Ivani,Oliveira, Roberta A.,Menezes, Paulo H.,De Freitas Filho, Joao R.
-
p. 10611 - 10620,10
(2012/12/12)
-
- Aluminium triflate catalysed O-glycosidation: Temperature-switched selective Ferrier rearrangement or direct addition with alcohols
-
A temperature-controlled mechanism switch between the Al(OTf) 3-catalysed direct addition of alcohols or the Ferrier rearrangement reactions in some glycals is presented. The scope and limitations are investigated as are the influence of the st
- Williams, D. Bradley G.,Simelane, Sandile B.,Kinfe, Henok H.
-
supporting information; experimental part
p. 5636 - 5642
(2012/08/07)
-
- Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions
-
Catalytic amounts of tellurium(IV) tetrachloride were used to promote the O-glycosylation of 3,4,6-tri-O-acetyl-d-glucal to give the corresponding 2,3-unsaturated-O-glycosides. With simple alcohols, the desired compounds were obtained in good yields and excellent anomeric selectivity in a short reaction time using only 2 mol % of the catalyst. The application of the method in the synthesis of a small set of glycopyranosides with rigid or flexible linkers gave the corresponding α anomers as products in good yields. Further applications of some of the synthesized compounds in allylation reaction of aldehydes gave the corresponding homoallylic alcohols in good yields.
- Freitas, Juliano C.R.,Couto, Túlio R.,Paulino, Ant?nio A.S.,De Freitas Filho, Jo?o R.,Malvestiti, Ivani,Oliveira, Roberta A.,Menezes, Paulo H.
-
p. 8645 - 8654
(2012/10/29)
-
- Iron(III) triflate, a new efficient catalyst for Type i Ferrier Rearrangement
-
By using iron(III) triflate as catalyst, an improved method for the synthesis of 2,3-unsaturated-O-glycosides has been established. A series of 2,3-unsaturated-O-glucosides were obtained from 2,4,6-tri-O-acetyl-d-glucal in good yield and high anomeric selectivity.
- Chen, Peiran,Wang, Shaoshan
-
supporting information; experimental part
p. 5356 - 5362
(2012/09/07)
-
- 2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies
-
The alarming resurgence of tuberculosis (TB) underlines the urgent need for development of new and potent anti-TB drugs. Towards this goal we herein report the design and synthesis of 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercula
- Saquib, Mohammad,Husain, Irfan,Sharma, Smriti,Yadav, Garima,Singh, Vipul K.,Sharma, Sandeep K.,Shah, Priyanka,Siddiqi, Mohammad Imran,Kumar, Brijesh,Lal, Jawahar,Jain, Girish K.,Srivastava, Brahm S.,Srivastava, Ranjana,Shaw, Arun K.
-
scheme or table
p. 2217 - 2223
(2011/06/22)
-
- Convertible formation of different glycoside using molecular iodine
-
The observation of convertible formation between 2-deoxy-2-iodo-O- glycosides and 2,3-unsaturated glycoside was described. The selective formation of 2-deoxy-2-iodo-O-glycosides was found from the reaction of D-glucal with iodine in the excess alcohol acceptor or the addition of ceric ammonium nitrate as additive while the addition of a stoichiometric amount of alcohol in solvent favored 2,3-unsaturated glycosides formation. The Japan Institute of Heterocyclic Chemistry.
- Saeeng, Rungnapha,Sirion, Uthaiwan,Sirichan, Yada,Trakulsujaritchok, Thanida,Sahakitpichan, Poolsak
-
experimental part
p. 2569 - 2580
(2011/04/22)
-
- A facile H2SO4/4 ? molecular sieves catalyzed synthesis of 2,3-unsaturated O -glycosides via ferrier-type rearrangement
-
A novel method for synthesizing 2,3-unsaturated glycosides has been developed using a metal-free catalytic system. This catalyst, sulfuric acid/4 molecular sieves can catalyze the reaction of 3,4,6-tri-O-acetyl-d-glucals and a wide range of alcohols at room temperature, affording 2,3-unsaturated glycosides in good -selectivity (α/β> 6:1) via a Ferrier-type rearrangement. Georg Thieme Verlag Stuttgart - New York.
- Zhou, Jiafen,Zhang, Bo,Yang, Guofang,Chen, Xuan,Wang, Qingbing,Wang, Zhongfu,Zhang, Jianbo,Tang, Jie
-
experimental part
p. 893 - 896
(2010/07/16)
-
- H2SO4-SiO2: Highly efficient and novel catalyst for the Ferrier-type glycosylation
-
Sulfuric acid immobilized on silica gel is designed as a very useful catalyst for synthesis of 2,3-unsaturated glycopyranosides. This handy, metal-free, environment friendly transformation provides high yields and α-stereoselectivities in a very few amount (0.02 eq.) of catalyst and in short reaction times (10 min).
- Zhou, Jia Fen,Chen, Xuan,Wang, Qing Bing,Zhang, Bo,Zhang, Li Yan,Yusulf, Abdullh,Wang, Zhong Fu,Zhang, Jian Bo,Tang, Jie
-
experimental part
p. 922 - 926
(2011/11/12)
-
- Kinetically controlled Ferrier rearrangement of 3-O-mesyl-d-glycal derivatives
-
The Ferrier rearrangement, which is widely used in carbohydrate chemistry, is generally performed under acidic conditions to give an α anomer with high stereoselectivity. We have found that 3-O-mesyl-d-glycals 2-4 were smoothly reacted with alcohols in th
- Watanabe, Yuhya,Itoh, Tsubasa,Sakakibara, Tohru
-
experimental part
p. 516 - 520
(2009/05/11)
-
- ZnCl2/alumina impregnation catalyzed Ferrier rearrangement: an expedient synthesis of pseudoglycosides
-
An improved method for the synthesis of 2,3-unsaturated-O-glycosides has been developed. ZnCl2 impregnated on activated alumina acts as an excellent reagent system for the conversion of 2,4,6-tri-O-acetyl-d-glucal to 2,3-unsaturated-O-glycosides with high α-selectivity.
- Gorityala, Bala Kishan,Lorpitthaya, Rujee,Bai, Yaguang,Liu, Xue-Wei
-
experimental part
p. 5844 - 5848
(2009/12/01)
-
- Synthesis of 2,3-unsaturated O- and N-glycosides by HBF4· SiO2-catalyzed ferrier rearrangement of D-glycals
-
Fluoroboronic acid adsorbed on silica gel (HBF4·SiO 2) catalyzes the Ferrier rearrangement of per-O-acetylated glycals with alcohols and sulfonamides to give 2,3-unsaturated O- and N-glycosides in good to excellent yield and with high α-stereoselectivity. Georg Thieme Verlag Stuttgart.
- Rodríguez, Oscar Mariano,Colinas, Pedro Alfonso,Bravo, Rodolfo Daniel
-
scheme or table
p. 1154 - 1156
(2009/10/17)
-
- Indium trichloride promoted stereoselective synthesis of O-glycosides from trialkyl orthoformates
-
A novel, highly stereoselective method for O-glycosylation of glycals and glycosylbromides is developed using orthoformates as acceptors in the presence of InCl3 to afford the corresponding O-glycopyranosides in 66-94% yield. Both perbenzyl and peracetyl glycals afford the corresponding 2,3-unsaturated-O-glycosides with high α-selectivity. Stoichiometric amounts of orthoformates are sufficient to bring about this transformation instead of large excesses of alcohols.
- Mukherjee, Debaraj,Yousuf, Syed Khalid,Taneja, Subhash C.
-
p. 4944 - 4948
(2008/09/21)
-
- Design of chiral auxiliaries for the allene ether Nazarov cyclization
-
A 1,3- or a 1,4-cis axial tert-butyldimethylsilyloxy substituent on the pyranose derived chiral auxiliary for the allene ether Nazarov cyclization leads to products in high optical purity. α-Pyranose and β-pyranose derived auxiliaries lead to enantiomeric products. Copyright
- Banaag, April R.,Tius, Marcus A.
-
p. 5328 - 5329
(2008/02/04)
-
- Diastereoselective synthesis of 2′,3′-dideoxy- β-C- glucopyranosides as intermediates for the synthesis of 2′,3′- dideoxy-β-D-glucopyranosyl-C-nucleosides
-
An extension of the Vorbrueggen method of nucleotide synthesis for the synthesis of C-glucopyranosides, as intermediates for C-nucleosides, is described. It could be shown that the diastereoselectivity of the reaction can be tuned by a simple change of protecting groups. Copyright Taylor & Francis Group, LLC.
- Loepfe, Michael,Siegel, Jay S.
-
p. 1029 - 1035
(2008/09/17)
-
- TRANSACETALISATION PROCESS
-
The invention relates to the resolution of racemic mixtures, and in particular to the separation of enantiomers of chiral alcohols utilising recyclable chiral auxiliaries. The present invention also relates to a process for preparing these recyclable chiral auxiliaries using an enantiomerically pure alcohol.
- -
-
Page/Page column 41-42
(2010/02/13)
-
- A new bismuth nitrate-induced stereospecific glycosylation of alcohols
-
Bismuth nitrate-catalyzed stereospecific glycosylation of alcohol with glycal has been developed.
- Banik, Bimal K.,Adler, Dorothy,Nguyen, Phuong,Srivastava, Neeta
-
p. 101 - 104
(2007/10/03)
-
- Synthesis of C7-C16-alkyl 2,3-dideoxy glucosides from glucose and fatty alcohols
-
C7-C16-alkyl 2,3-dideoxy glucosides have been synthesized from glucose and C7-C16-alkanols by Ferrier reaction using boron trifluoride etherate (BF3·Et2O) as Lewis acid catalyst in key step.
- Konstantinovic,Predojevic,Gojkovic,Ratkovic,Mojsilovic,Pavlovic
-
p. 1242 - 1244
(2007/10/03)
-
- Indium trichloride catalyzed glycosidation. An expeditious synthesis of 2,3-unsaturated glycopyranosides
-
Treatment of tri-O-acetyl-D-glucal 1 with various alcohols and phenols in the presence of InCl3/CH2Cl2 at ambient temperature gave the corresponding alkyl and aryl 2,3-unsaturated glycopyranosides in excellent yields with short reaction times and good anomeric selectivity. (C) 2000 Elsevier Science Ltd.
- Sobhana Babu, Boga,Kuppuswamy Balasubramanian, Kalpattu
-
p. 1271 - 1274
(2007/10/03)
-
- Lithium tetrafluoborate catalyzed ferrier rearrangement - Facile synthesis of alkyl 2,3-unsaturated glycopyranosides
-
Treatment of tri-O acetyl-D-galactal 1 and tri-O-acetyl-D-glucal 2 with diverse alcohols in the presence of LiBF4 in CH3CN, furnished alkyl, 2,3- unsaturated glycopyranosides 3-18 (50-86%).
- Sobhana Babu,Balasubramanian
-
p. 4299 - 4305
(2007/10/03)
-
- Simple Designs for the Construction of Complex Trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations
-
A successful design for the construction of trans-fused medium-size cyclic ethers is described.The key features of the synthesis are as follows: (i) intramolecular oxirane ring expansion in cycloalkenes to give bridged oxabicyclic systems and (ii) linear, one- or two-directional synthetic operations which generate external oxocycles in single reaction steps.The general approach involves the intramolecular addition of a stable γ-alkoxy-substituted allylstannane to an aldehyde carbonyl group, and the entire reaction is conducted in a one-pot process which includes the following: (i) vic-diol fragmentation from the bridged oxabicyclic precursor and (ii) Lewis acid-induced cyclization of the resulting aldehyde-allylic tin system.While the present strategy was mostly developed around racemic models, the potential for adoption of enantioselective features is immediate.The versatility, scope, limitations, and potential applications of the present technology are discussed in detail.
- Alvarez, Eleuterio,Diaz, Maria T.,Perez, Ricardo,Ravelo, Jose L.,Regueiro, Alicia,et al.
-
p. 2848 - 2876
(2007/10/02)
-
- Efficient Preparation of Intermediates Corresponding to C22-C27 and C28-C34 of FK-506
-
Efficient large-scale preparations of aldehyde 2 and sulfone 3 representing the C22-C27 and C28-C34 potions of the immunosuppressant FK-506 (1) are descibed.
- Linde, II Robert G.,Egbertson, Melissa,Coleman, Robert S.,Jones, A. Brian,Danishefsky, Samuel J.
-
p. 2771 - 2776
(2007/10/02)
-
- The facile conversion of pyranoid glycals into 2-deoxy-glycosidic orthoesters
-
The formation of 2-deoxy-glycosidic orthoesters involving the palladium(II) catalysed reaction of pyranoid glycals with alcohols in the presence of sodium hydrogen carbonate is described.
- Holzapfel, Cedric W.,Engelbrecht, Gerhardus J.,Verdoorn, Gerhard H.
-
p. 433 - 444
(2007/10/02)
-
- SYNTHESIS AND STEREOCHEMICAL CHARACTERIZATION OF OPTICALLY ACTIVE 2-METHOXY-3,4-DIHYDRO-2H-PYRAN
-
Samples of (+)-2-methoxy-3,4-dihydro-2H-pyran (1) have been prepared starting from methyl α-D-glucopyranoside and from tri-O-acetyl-D-glucal; the absolute configuration as well as the maximum rotatory power of 1 have been established.
- Menicagli, Rita,Malanga, Corrado,Pecunioso, Angelo,Lardicci, Luciano
-
-
- Vers la synthese totale de la d,l-desosamine. Formation du carbon anomere au moyen de PhSeBr
-
Reaction of phenylselenyl bromide with dihydropyrans in the presence of methanol, followed by oxidative elimination, leads to α,β-unsaturated acetals.This method, which constitutes a new way for generating an anomeric center in the total synthesis of hexopyranose derivatives, has been applied towards the synthesis of methyl 3,4,6-trideoxy-3-dimethylamino-D,L-xylo hexopyranoside (methyl D,L-desosamide).
- Berube, Gervais,Luce, Eric,Jankowski, Krzysztof
-
p. 109 - 111
(2007/10/02)
-
- PALLADIUM-ASSISTED CARBOHYDRATE REACTIONS I. SODIUM CYANOBOROHYDRIDE-PROMOTED ALLYLIC REARRANGEMENTS OF C-6 SUBSTITUTED PYRANOSIDE GLYCALS.
-
Methoxypalladation of C-6 substituted pyranoside glycals followed by addition of sodium cyanoborohydride gives allylic rearrangement products in good yield with excellent regio- and stereoselectivity.
- Dunkerton, Lois V.,Brady, Kevin T.,Mohamed, Farhana
-
p. 599 - 602
(2007/10/02)
-