73366-73-1Relevant articles and documents
One-pot synthesis of orthogonally protected sugars through sequential base-promoted/acid-catalyzed steps: A solvent-free approach with self-generation of a catalytic species
Traboni, Serena,Bedini, Emiliano,Giordano, Maddalena,Iadonisi, Alfonso
supporting information, p. 1777 - 1780 (2019/06/07)
A varied set of solvent-free, one-pot synthetic sequences were developed to carry out the orthogonal protection of saccharide polyols. These sequences are composed of an initial regioselective benzylation, silylation or iodination (under mildly basic cond
Introduction of 4-Chlorophenyl: A Protecting Group for the Hydroxy Function
Otsuka, Yuji,Yamamoto, Toshihiro,Fukase, Koichi
supporting information, p. 1510 - 1516 (2018/04/24)
4-Chlorophenyl ether was utilized as a new protecting group for the hydroxy function. This group was readily introduced to a sugar hydroxy group by using diaryliodonium triflate. Regioselective introduction of this protecting group at the vicinal cis -diol was achieved by using a copper catalyst and diaryliodonium triflate. This protecting group is stable under the Lewis acidic conditions of glycosylation, but it can be readily removed by the initial conversion into the corresponding 4-methoxyphenyl ether with use of a Pd catalyst, followed by oxidation with ammonium cerium (IV) nitrate [(NH 4) 2 Ce(NO 3) 6 ] (CAN).
Synthesis of |β-(1→2)-linked oligomannosides
Polakova, Monika,Roslund, Mattias U.,Ekholm, Filip S.,Saloranta, Tiina,Leino, Reko
experimental part, p. 870 - 888 (2009/07/17)
β-(1→2)-Linked oligomannosides constitute an important class of carbohydrate structures located on the cell surface of several Candida species, including C. albicans. As a result of the immunostimulating properties of such compounds, the upscaling of their synthesis is relevant. In this paper, a highly stereoselective synthesis of |β-(1→2)-linked oligomannosides was performed by further development of and modifications to the methodologies described earlier in the literature. In addition to the synthesis of fully deprotected β-(1→2)-linked mannobiose and mannotriose, some preliminary modifications to the oligosaccharide core, resulting in close analogues with biological potential, are presented. The fully deprotected products form potential targets for screening against C. albicans and may also result in new model structures for vaccine development.
Synthesis of DIvalent 2,2′-linked mannose derivatives by homodimerization
Ekholm, Filip S.,Polakova, Monika,Pawlowicz, Agnieszka J.,Leino, Reko
experimental part, p. 567 - 576 (2009/07/18)
Several studies have implicated (1 → 2)-linked mannans as biologically relevant compounds. Recently, there has been a growing interest in the synthesis of multivalent carbohydrate assemblies due to their ability to target multiple receptors simultaneously. In the present work, a protective group strategy, based on the methodology originally developed by Crich, has been utilized for the homodimerization of olefinic carbohydrates, allowing a highly diastereoselective synthesis of some divalent structures. Furthermore, it is shown that divalent donors may undergo coupling reactions without losses in stereoselectivity or efficiency. The strategies described may potentially be applied to the synthesis of diverse neoglycoconjugates and oligosaccharides. Georg Thieme Verlag Stuttgart.
Highly efficient chemoenzymatic synthesis of naturally occurring and non-natural α-2,6-linked sialosides: A P. damsela α-2,6- sialyltransferase with extremely flexible donor-substrate specificity
Yu, Hai,Huang, Shengshu,Chokhawala, Harshal,Sun, Mingchi,Zheng, Haojie,Chen, Xi
, p. 3938 - 3944 (2007/10/03)
(Chemical Equation Presented) Just relax: A one-pot, three-enzyme chemoenzymatic synthetic approach is highly efficient for obtaining complex sialosides that contain diverse naturally occurring sialic acid modifications. α-2,6-Linked sialosides containing
Total synthesis of bleomycin A2 and related agents. 4. Synthesis of the disaccharide subunit: 2-O-( 3-O-Carbamoyl-α-D-mannopyranosyl)-L-gulopyranose and completion of the total synthesis of bleomycin A2
Boger, Dale L.,Honda, Takeshi
, p. 5647 - 5656 (2007/10/02)
The chemical synthesis of 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose and its incorporation into a total synthesis of bleomycin A2 (1) readily adaptable to the preparation of structural analogs are detailed. Key strategic elements of
CHEMO-, STEREO- AND REGIOSELECTIVE HYDROGENOLYSIS OF CARBOHYDRATE BENZYLIDENE ACETALS. SYNTHESIS OF BENZYL ETHERS OF BENZYL α-D-, METHYL β-D-MANNOPYRANOSIDES AND BENZYL α-D-RHAMNOPYRANOSIDE BY RING CLEAVAGE OF BENZYLIDENE DERIVATIVES WITH THE LiAlH4-AlCl3
Liptak, Andras,Imre, Janos,Harangi, Janos,Nanasi, Pal,Neszmelyi, Andras
, p. 3721 - 3728 (2007/10/02)
Treatment of benzyl α-(1) and methyl β-D-mannopyranoside (2) with α,α-dimethoxytoluene gave the exo and endo isomers (3,5 and 4,6) of the dibenzylidene derivatives of 1 and 2.Hydrogenolysis of the exo isomers (3 and 5) with a molar equivalent of AlH2Cl ga
