120132-10-7Relevant articles and documents
Anomeric sugar boronic acid analogues as potential agents for boron neutron capture therapy
Imperio, Daniela,Del Grosso, Erika,Fallarini, Silvia,Lombardi, Grazia,Panza, Luigi
, p. 1355 - 1359 (2019)
After the development of accelerators as neutron source, the access to new suitable agents for boron neutron capture therapy (BNCT) became a major need. Among many others, sugar boronic acids have recently attracted attention as boron carriers. Herein we
Diversity-Oriented Synthesis of Carbohydrate Scaffolds through the Prins Cyclization of Differently Protected d-Mannitol-Derived Homoallylic Alcohols
Dubbu, Sateesh,Vankar, Yashwant D.
, p. 5986 - 6002 (2017/11/14)
A diversity-oriented synthesis of a variety of carbohydrate scaffolds, including sugar-fused isochroman derivatives, bicyclic vinyl halide derivatives, fluorine-substituted tetrahydropyrans, and a furan derivative, is reported. This was achieved through the Prins reaction of d-mannitol-derived homoallylic alcohols in which the allylic alcohol bears a different protecting group, leading to structural variation in the products. Some of the products were also converted into more functionalized scaffolds of wider utility and of possible biological importance. Appropriate mechanisms have been proposed to account for the product formation.
Synthesis of substituted tetrahydrofuran by electrophile-induced cyclization of 4-pentene-1,2,3-triols - An example of 5-exo versus 5-endo cyclization governed by the electrophile
Bravo, Fernando,Castillon, Sergio
, p. 507 - 516 (2007/10/03)
Differently protected 4-pentene-1,2,3-triols 5-8 were obtained from glyceraldehyde and submitted to iodine-based electrophile-induced cyclization to give tetrahydrofuran derivatives 10 and 18, with high chemo-, regio-, and stereo-selectivity, through a 5-exo cyclization process. However, when an electrophilic selenium reagent was treated with similar alkene triols 5, 7, and 8, the product depended on the protecting group at the primary hydroxy moiety. Thus, while compounds 5a and 5b, unprotected at the primary hydroxy group, give compounds 26 and 27, and 32 and 33, respectively, through a 5-exo cyclization process, compounds 7 and 8, protected at the primary hydroxy group, give the 5-endo cyclization products 22-25 and 28-31 in good yields. The electrophile-induced cyclization of 4-pentene-1,2,3-triols to give tetrahydrofuran derivatives can be directed towards a 5-exo process by the use of iodine or, when the primary hydroxy group is unprotected, selenium. When the primary hydroxy group is protected, use of selenium results in 5-endo cyclization.
Synthesis of erythro and threo furanoid glycals using 5-endo-trig selenoetherification as key step
Bravo,Kassou,Castillon
, p. 1187 - 1190 (2007/10/03)
Differently protected erythro and threo furanoid glycals were synthesised from 4-pentene-1,2,3-triol, through selenium induced 5-endo-trig cyclization and selenoxide elimination.
A NEW SYNTHETIC METHOD FOR γ-BUTYROLACTOLS BY THE PALLADIUM-CATALYZED REGIOSELECTIVE OXIDATION OF 1-ALKEN-4-OLS
Nokami, Junzo,Ogawa, Hideki,Miyamoto, Shinya,Mandai, Tadakatsu,Wakabayahi, Shoji,Tsuji, Jiro
, p. 5181 - 5184 (2007/10/02)
3-substituted 1-alken-4-ols were oxidized with PdCl2-benzoquinone regioselectively at the terminal carbon to afford cyclic hemiacetals (γ-butyroacetols), which were converted to γ-butiroacetones by the Jones oxidation.This reactions was applied to the synthesis of optically active deoxyribose and γ-butenolides.
