6087-41-8Relevant articles and documents
General Strategy for the Synthesis of Rare Sugars via Ru(II)-Catalyzed and Boron-Mediated Selective Epimerization of 1,2- trans-Diols to 1,2- cis-Diols
Li, Xiaolei,Tang, Weiping,Wu, Jicheng
supporting information, p. 3727 - 3736 (2022/03/02)
Human glycans are primarily composed of nine common sugar building blocks. On the other hand, several hundred monosaccharides have been discovered in bacteria and most of them are not readily available. The ability to access these rare sugars and the corresponding glycoconjugates can facilitate the studies of various fundamentally important biological processes in bacteria, including interactions between microbiota and the human host. Many rare sugars also exist in a variety of natural products and pharmaceutical reagents with significant biological activities. Although several methods have been developed for the synthesis of rare monosaccharides, most of them involve lengthy steps. Herein, we report an efficient and general strategy that can provide access to rare sugars from commercially available common monosaccharides via a one-step Ru(II)-catalyzed and boron-mediated selective epimerization of 1,2-trans-diols to 1,2-cis-diols. The formation of boronate esters drives the equilibrium toward 1,2-cis-diol products, which can be immediately used for further selective functionalization and glycosylation. The utility of this strategy was demonstrated by the efficient construction of glycoside skeletons in natural products or bioactive compounds.
Practical synthesis of 2-deoxy sugars via metal free deiodination reactions
Yao, Wang,Wang, Hao,Zeng, Jing,Wan, Qian
, p. 454 - 478 (2022/01/20)
2-Deoxy-glycosides, in which the C-2 hydroxyl group is replaced with a hydrogen atom, are important motifs in numerous bioactive natural products and pharmaceutical molecules. Herein, an improved dilauroyl peroxide-mediated radical deiodination reaction b
A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light to Synthesize Deoxyglycosides
Ge, Jian-Tao,Zhou, Lang,Luo, Tao,Lv, Jian,Dong, Hai
supporting information, p. 5903 - 5906 (2019/08/26)
We herein developed an efficient method for removing thioacetyl to synthesize acylated deoxy glycosides in a one-pot reaction, where the thioacetyl was selectively deacetylated by hydrazine hydrate in DMF within 2-5 min at room temperature, followed by de
TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
Hsu, Mei-Yuan,Liu, Yi-Pei,Lam, Sarah,Lin, Su-Ching,Wang, Cheng-Chung
supporting information, p. 1758 - 1764 (2016/10/05)
The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.
Ferrier rearrangement and 2-deoxy sugar synthesis from d-glycals mediated by layered α-zirconium sulfophenylphosphonate-methanphosphonate as heterogeneous catalyst
Rosati, Ornelio,Curini, Massimo,Messina, Federica,Marcotullio, Maria Carla,Cravotto, Giancarlo
, p. 169 - 175 (2013/03/13)
Layered α-zirconium sulfophenylphosphonate-methanphosphonate is a solid acid catalyst that catalyzes Ferrier rearrangement from d-glycals and alcoholic nucleophiles under mild reaction conditions in short time and good yields. Notably, the combination of α-zirconium sulfophenylphosphonate- methanphosphonate and lithium bromide change the regioselectivity of this process affording 2-deoxy sugars in good yields. Graphical Abstract: [Figure not available: see fulltext.]
A chiron approach to (-)-tetrahydrolipstatin
Yadav,Vishweshwar Rao,Prasad
, p. 3888 - 3894 (2008/02/09)
An efficient chiron approach to the total synthesis of (-)- tetrahydrolipstatin is described. The main features of the synthetic strategy, which starts from tri-O-acetyl-D-glucal, are copper-mediated C-C bond formation, Frater alkylation, and Barton-McCombie deoxygenation. Georg Thieme Verlag Stuttgart.
Synthetic studies on antascomicin A: Construction of the C18-C34 fragment
Fuwa, Haruhiko,Okamura, Yumiko,Natsugari, Hideaki
, p. 5341 - 5352 (2007/10/03)
Stereoselective synthesis of the C18-C34 fragment of antascomicin A is described. Construction of the C27-C34 carbocycle moiety was achieved via catalytic Ferrier carbocylization and Johnson-Claisen rearrangement, which was converted to iodide 2 by use of
Synthesis of a-ring synthon of 19-nor-1alpha,25-dihydroxyvitamin D3 from (D)-glucose
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Page 5-6, (2010/02/07)
The present invention provides a method for the synthesis of an A-ring synthon phosphine oxide used in the preparation of 19-nor vitamin D compounds, and to novel synthetic intermediates formed during the synthesis. The new method prepares the phosphine oxide from (D)-glucose.
Novel synthesis of 2-substituted 19-norvitamin D A-ring phosphine oxide from D-glucose as a building block
Shimizu, Masato,Iwasaki, Yukiko,Shibamoto, Yoshinori,Sato, Miki,DeLuca,Yamada, Sachiko
, p. 809 - 812 (2007/10/03)
19-Norvitamin D A-ring phosphine oxide 5 was synthesized by a new sequence mode starting from D-glucose as a chiral template. Transformation of the pyranoside ring into the A-ring carbocycle was achieved by the Pd-catalyzed Ferrier rearrangement. The phosphine oxide 5 was obtained in an 18% overall yield by this novel cost-effective method.
Indium-mediated stereospecific glycosylation of alcohols
Banik, Bimal K.,Samajdar, Susanta,Indrani, Banik,Zegrocka, Oliwia,Becker, Frederick F.
, p. 227 - 230 (2007/10/03)
Indium has been shown to be effective in the stereospecific glycosylation of various alcohols with bromosugars.