13265-84-4Relevant articles and documents
Cesium carbonate-promoted Michael-type addition of thiols to hex-1-en-3-ulose: A practical synthesis of 2-deoxy-1-thio-α-hexopyranosid- 3-ulose template
Ganguly, Debashis,Tang, Haiqun,Rodriguez, Michael J.
, p. 4219 - 4226 (2007)
The template 2-deoxy-1-thio-α-hexopyranosid-3-ulose was synthesized in quantitative yield and high diastereoselectivity by 1,4-addition of aryl and alkyl thiols to hex-1-en-3-ulose promoted by cesium carbonate in THF. Copyright Taylor & Francis Group, LLC
Studies directed toward the total synthesis of Scytophycin C: Synthesis of the C(1)-C(18) fragment of Scytophycin C
Grieco, Paul A.,Speake, Jason D.
, p. 1275 - 1278 (1998)
The synthesis of the C(1) to C(18) fragment of Scytophycin C is described which features a highly stereoselective carbon Ferrier-type reaction in 3.0 M lithium perchlorate/ethyl acetate.
C-glycosides and C-disaccharide precursors through carbonylative stille coupling reactions
Jeanneret, Vincent,Meerpoel, Lieven,Vogel, Pierre
, p. 543 - 546 (1997)
Under CO atmosphere and in the presence of Pd2(dba)3 and Ph3As a suitably protected 1-stannylglucal derivative could be carbonylated and coupled to 5-bromo-7-oxabidyclo[2.2.1]hept-5-en-2-yl derivatives. The carbonylative Stille coupling was also successful between 1-iodoglucals and tributyl(vinyl)stannane or tributyl(fur-2-yl)stannane. A cross-conjugated dienone was also obtained through coupling of a 1-stannylglucal with a 1-iodoglucal derivative.
A concise, enantioselective synthesis of (+)-decarestrictine L from Tri-O-acetyl-D-glucal
Zuniga, Andrea,Perez, Manuel,Pazos, Gonzalo,Gomez, Generosa,Fall, Yagamare
, p. 2446 - 2450 (2010)
We describe a new and efficient approach to the enantioselective synthesis of (+)-(2R,3S,6R)-decarestrictine L from commercially available tri-O-acetyl-D-glucal, based on a stereoselective Michael addition. Georg Thieme Verlag Stuttgart · New York.
Enantioselective Synthesis of Spliceostatin G and Evaluation of Bioactivity of Spliceostatin G and Its Methyl Ester
Ghosh, Arun K.,Reddy, Guddeti Chandrashekar,MacRae, Andrew J.,Jurica, Melissa S.
, p. 96 - 99 (2018)
An enantioselective total synthesis of spliceostatin G has been accomplished. The synthesis involved a Suzuki cross-coupling reaction as a key step. The functionalized tetrahydropyran ring was constructed from commercially available optically active tri-O-acetyl-d-glucal. Other key reactions include a highly stereoselective Claisen rearrangement, a Cu(I)-mediated 1,4 addition of MeLi to install the C8 methyl group, and a reductive amination to incorporate the C10 amine functionality of spliceostatin G. Biological evaluation of synthetic spliceostatin G and its methyl ester revealed that it does not inhibit splicing in vitro.
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Hehre et al.
, p. 1780,1781-1785 (1977)
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Convenient Synthesis of Hex-1-enopyran-3-uloses: Selective Oxidation of Allylic Alcohols Using Pyridinium Dichromate
Czernecki, S.,Vijayakumaran, K.,Ville, G.
, p. 5472 - 5475 (1986)
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ADDITION OF HALOGENOAZIDES TO GLYCALS
Bovin, Nicolai V.,Zurabyan, Sergei E.,Khorlin, Anatoly Y.
, p. 25 - 36 (1981)
Addition of chloroazide to 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-lyxo- (1) and -D-arabino-hex-1-enitol (2) under u.v. irradiation proceeds regio- and stereo-selectively yielding mainly O-acetyl derivatives of 2-azido-2-deoxy-D-galactopyranose and -D-glucopyranose, respectively. 3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl azide and 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-talopyranose (from 1), and 1,3,4,6-tetra-O-acetyl-2-chloro-2-deoxy-α-D-glucopyranosyl azide and 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranose (from 2) are byproducts. 1,5-Anhydro-3,4,6-tri-O-benzyl-2-deoxy-D-lyxo- and -D-arabino-hex-1-enitol reacted more rapidly with chloroazide, to give, under irradiation, derivatives of 2-azido-2-deoxy-D-galactose and -D-glucose, respectively.However, reaction in the dark gave mainly O-benzyl derivatives of 2-chloro-2-deoxy-α-D-galacto- and -α-D-glucopyranosyl azide.The difference between the products obtained may depend on the existence of two parallel processes, one radical (under irradiation), and the other ionic (reaction in the dark).
Synthesis of 2′-paclitaxel 2-deoxy-2-fluoro-glucopyranosyl carbonate for specific targeted delivery to cancer cells
Li, Tingshen,Li, Xiao,Lian, Xujing,Meng, Xin,Ya, Qiang,Yang, Yang,Zhang, Yan,Zhang, Yongmin
, (2020)
A novel 2-fluorodeoxyglucose conjugated derivative of paclitaxel was efficiently synthesized using a linker between 2′-OH of paclitaxel and C1-hydroxyl group of 2-fluorodeoxyglucose. In preparation of the prodrug, allyl carbonates were selected as the protective group and the efficient one-step removal of allyloxycarbonyl groups at the end of the synthesis using palladium chemistry gave the target molecule in good yield. The prodrug not only improved the pharmaceutical properties of paclitaxel, such as solubility and stability, but also demonstrated enhanced cytotoxicity and selectivity for cancer cells and less toxicity toward normal HUVEC cells.
1-[2-(Trimethylsilyl)ethoxy]ethyl (SEE): A novel hybrid hydroxy-protecting group between 1-(ethoxy)ethyl (EE) and 2-(trimethylsilyl)ethoxymethyl (SEM)
Wu, Junjun,Shull, Brian K.,Koreeda, Masato
, p. 3647 - 3650 (1996)
The highly versatile 1-[(2-trimethylsilyl)ethoxy]ethyl (SEE) group, readily obtainable from an alcohol and 2-(trimethylsilyl)ethyl vinyl ether in the presence of a catalytic amount of PPTS, has been developed for the protection of hydroxyl groups. Its deprotection can be achieved under virtually neutral conditions with the use of a fluoride ion source, thus allowing for effective protection of hydroxyl groups of compounds that contain acid- and/or base-sensitive functional groups.
An electrophile-mediated cyclization on the 1,6-anhydro-D-glucopyranose framework
Leteux, Christine,Veyrieres, Alain,Robert, Francis
, p. 119 - 130 (1993)
Iodocyclization of O-tributylstannyl-D-glucal with iodine in acetonitrile gave 1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose (1) in high yield.The 3,4-di-O-acetyl derivative of 1 could be converted into the corresponding 2-deoxy compound and into the 2-C-allyl-2-deoxy branched sugar (5) by treatment with tributylstannane and allyltributylstannane, respectively.Controlled alkaline hydrolysis of 5 gave the 4-monoacetyl derivative.Complete hydrolysis of 5 gave the 3,4-diol, which underwent a 5-exo cyclization by treatment with N-bromosuccinimide. 1H NMR spectroscopy and X-ray analysis showed that the cyclized product has the B3,0 conformation in its pyranose ring, which is trans-fused to the newly formed tetrahydrofuran ring.
Aziridine Ring Opening as Regio-and Stereoselective Access to C-Glycosyl-Aminoethyl Sulfide Derivatives
Le?niak, Stanis?aw,Malinowska, Martyna,Tracz, Aleksandra,Zawisza, Anna
, (2022/03/23)
A short synthetic route to stereoselective access to C-glycosyl-aminoethyl sulfide derivatives has been developed through the reaction of tributhyltin derivatives of glycals with aziridinecarboaldehyde and the regioselective ring opening of a chiral aziridine with thiophenol. The absolute configurations of the resulting diastereoisomers were determined by 1H NMR spectroscopy.
Method for efficiently constructing 1, 2-cis-2-nitro-glucoside and galactoside
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Paragraph 0038; 0063; 0064, (2021/08/11)
The invention discloses a method for efficiently constructing 1, 2-cis-2-nitro-glucoside and 1, 2-cis-2-nitro-galactoside, and belongs to the technical field of organic synthesis. According to the preparation method, the 1, 2-cis-2-nitro-glucoside and the 1, 2-cis-2-nitro-galactoside can be efficiently prepared through one-step synthesis. According to the present invention, the organic catalysis stereoselective glycosylation method is successfully applied to the sugar chemical total synthesis so that the problem of the construction of the 1, 2-cis-glucosidic bond between the most key sugar units is solved, and the foundation is established for the completion of the subsequent poly O-antigen total synthesis. The work has important reference value for related immunological research and vaccine development in the future.
Development of Routes for the Stereoselective Preparation of β-Aryl- C-glycosides via C-1 Aryl Enones
Kanaujiya, Vimlesh Kumar,Kandasamy, Jeyakumar,Sabiah, Shahulhameed,Singh, Adesh Kumar,Tiwari, Varsha
supporting information, p. 7650 - 7655 (2020/10/09)
A wide range of enones derived from d-glucal, d-galactal, l-rhamnal, d-rhamnal, and l-arabinal underwent Heck-coupling with various arylboronic acids bearing electron-donating and -withdrawing groups in the presence of palladium acetate and 1,10-phenanthroline. These reactions provided synthetically useful C-1 aryl enones in good yields. Many sensitive functional groups as well as protecting groups present in arylboronic acids and enones, respectively, remained intact under optimized conditions. The stereoselective hydrogenation of C-1 aryl enones with Pd-C/H2 provides the β-isomer of 2-deoxy-aryl-C-glycosides in excellent yield. The C-1 aryl enones were also used as precursors for the synthesis of 2-hydroxy-β-aryl-C-glycosides. Regioselective C-2 halogenations and vinylations of C-1 aryl enones were achieved in excellent yields.
