135145-83-4Relevant academic research and scientific papers
Cross-coupling reaction of saccharide-based alkenyl boronic acids with aryl halides: The synthesis of bergenin
Parkan, Kamil,Pohl, Radek,Kotora, Martin
, p. 4414 - 4419 (2014/05/06)
A convenient synthetic pathway enabling D-glucal and D-galactal pinacol boronates to be prepared in good isolated yields was achieved. Both pinacol boronates were tested in a series of cross-coupling reactions under Suzuki-Miyaura cross-coupling conditions to obtain the corresponding aryl, heteroaryl, and alkenyl derivatives in high isolated yields. This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandin D and the first total synthesis of bergenin. Building blocks with boron: A convenient synthetic route to D-glucal and D-galactal pinacol boronates was developed, and the boronates were used in cross-coupling reactions to generate the corresponding aryl, heteroaryl, and alkenyl derivatives in high yields (see scheme). This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandin D and the total synthesis of bergenin.
Aryl-β-C-glucosidation using glucal boronate: Application to the synthesis of tri-O-methylnorbergenin
Sakamaki, Shigeki,Kawanishi, Eiji,Nomura, Sumihiro,Ishikawa, Tsutomu
, p. 5744 - 5753 (2012/09/08)
Novel aryl-β-C-glucosidation method using glucal boronate was developed. This protocol can offer several advantages including use of non-toxic, easily handling glucal boronate as a crystalline solid and storable at room temperature for several months. Tri-O-methylnorbergenin (8,10-di-O-methylbergenin), an anti-HIV active bergenin derivative, was concisely synthesized by application of the aryl-β-C-glucosidation method.
Remarkable oxidation stability of glycals: Excellent substrates for cerium(IV)-mediated radical reactions
Linker, Torsten,Schanzenbach, Dirk,Elamparuthi, Elangovan,Sommermann, Thomas,Fudickar, Werner,Gyollai, Viktor,Somsak, Laszlo,Demuth, Wolfgang,Schmittel, Michael
supporting information; experimental part, p. 16003 - 16010 (2009/05/15)
The remarkable stability of glycals under oxidative conditions becomes apparent by their redox data in solution, computed HOMO energies, and behavior on the addition of electrophilic radicals generated in the presence of cerium(IV) ammonium nitrate. Oxida
The preparation of C-aryl glucals via palladium-catalyzed cross-coupling methods
Friesen,Loo,Sturino
, p. 1262 - 1272 (2007/10/02)
The C-aryl glucals 17-31 have been prepared by the palladium-catalyzed cross coupling of 1-tributylstannyl-3,4,6-tri-O-(tert-butyldimethylsilyl)-b-glucal (11) and aryl bromides. The major by-product in all of these reactions is the dimer 33, the product o
Preparation of C-Aryl Glucals via the Palladium-Catalyzed Coupling of Metalated Aromatics with 1-Iodo-3,4,6-tri-O-(triisopropylsilyl)-D-glucal
Friesen, Richard W.,Loo, Richard W.
, p. 4821 - 4823 (2007/10/02)
The preparation of the novel iodo glucal 5 from 3,4,6-tri-O-(triisopropylsilyl)-D-glucal (4), via a two-step procedure involving C1 stannylation and subsequent tin-iodine exchange, is described.The palladium-catalyzed coupling of 5 with a variety of metal
