720698-24-8Relevant academic research and scientific papers
B(C6F5)3-Catalyzed Chemoselective Defunctionalization of Ether-Containing Primary Alkyl Tosylates with Hydrosilanes
Chatterjee, Indranil,Porwal, Digvijay,Oestreich, Martin
, p. 3389 - 3391 (2017)
Catalytic C(sp3)?O bond cleavage promoted by B(C6F5)3 /Et3SiH proceeds preferentially with primary tosylates in the presence of primary and secondary silyl ethers and aryl ethers. This reactivity difference enables the chemoselective defunctionalization of several 1,n-diols, and the efficiency of the new procedure is highlighted by the selective deoxygenation of the hydroxymethyl group of an orthogonally protected carbohydrate. Tosylates with an adjacent phenyl group are cleaved with anchimeric assistance.
Synthesis of novel sugar-lactam conjugates using the Aube reaction
Kurhade, Suresh E.,Mengawade, Tanaji,Bhuniya, Debnath,Palle, Venkata P.,Reddy, D. Srinivasa
, p. 744 - 747 (2011/04/16)
An efficient and convenient method for the synthesis of sugar-lactam conjugates is reported starting from readily available sugar azides using the Aube reaction. Cyclic azido alcohols are used in the Aube reaction for the first time in a carbohydrate setting. The resulting glycoconjugates could be further used to increase the chemical diversity on the sugar backbone, and may find potential applications as glycomimetics, peptidomimetics, in glycotargeting and in CNS drug delivery.
Identifying specific conformations by using a carbohydrate scaffold: Discovery of subtype-selective LPA-receptor agonists and an antagonist
Tamaruya, Yoko,Suzuki, Masato,Kamura, Goshu,Kanai, Motomu,Hama, Kotaro,Shimizu, Kumiko,Aoki, Junken,Arai, Hiroyuki,Shibasaki, Masakatsu
, p. 2834 - 2837 (2007/10/03)
Stable and potent subtype-selective lysophosphatidic acid (LPA) analogues (agonists and an antagonist) were developed by using carbohydrates as a core structure (see scheme). An array of molecules with the recognition motifs of LPA (a phosphate anion, an oleoyl group, and a hydrogen-bond acceptor) attached to carbohydrate isomers in different three-dimensional arrangements were tested for LPA-receptor activation or inhibition. R = alkyl.
Anti- and syn-selective cyanosilylation reactions promoted by a sugar-based bifunctional catalyst: Stereoselective syntheses of essential building blocks for HIV protease inhibitors and bestatin
Manickam, Govindaswamy,Nogami, Hiroyuki,Kanai, Motomu,Gr?ger, Harald,Shibasaki, Masakatsu
, p. 617 - 620 (2007/10/03)
Chiral bifunctional catalyst 6 promoted anti- and syn-selective cyanosilylation reactions from chiral amino aldehydes derived from phenylalanine in excellent yields. Thus, from dibenzyl protected amino aldehyde 9, syn isomer was obtained as the major prod
Biomimetic cyclisation of prebrevetoxin polyepoxide models
Kelly, David R.,Nally, James
, p. 3251 - 3254 (2007/10/03)
(E)-1,3-Dihydroxyhex-4-ene and (E)-1,3-dihydroxy-4-methylhex-4-ene undergo epoxidation with peracetic acid and in situ cyclisation to give a mixture of tetrahydro-furans and -pyrans, whereas comparable compounds lacking the allylic hydroxyl group give pre
