134038-73-6Relevant articles and documents
Organocatalytic syn-aldol reactions of hydroxy ketones with (S)-isoserinal: Asymmetric synthesis of 6-deoxy-1,5-iminohexitols and related compounds
Nicolas, Cyril,Pluta, Roman,Pasternak-Suder, Monika,Martin, Olivier R.,Mlynarski, Jacek
, p. 1296 - 1305 (2013/04/10)
An improved and convenient preparation of protected (S)-isoserinal on a large scale is reported. This key intermediate was reacted through organocatalyzed aldol reaction or Wittig based chain extension and functionalization to give enantiopure 1,5,6-trideoxy-1,5-imino-hexitols such as 10a (L-manno) and 10b (D-gluco). These two compounds are of interest as glycosidase inhibitors. The elaborated organocatalytic process includes diastereoselective syn aldol reaction of (S)-isoserinal hydrate and hydroxyacetone or 1-hydroxy-2-octanone and is promoted by various amino acid-based catalysts. Diastereoselectivities of up to 8:1 were achieved, thus establishing a new, efficient synthetic route to these important carbohydrate mimics. A novel protocol for the preparation of 1,5,6-trideoxy-1,5-imino-L- mannitol and 1,5,6-trideoxy-1,5-imino-D-glucitol is reported. The key steps include organocatalyzed syn-selective direct aldol reaction of hydroxyacetone and CBz-protected isoserinal hydrate, followed by reductive amination/ cyclization. Copyright
Total synthesis of the biphenomycins; II. Synthesis of protected (2S,4R)-4-hydroxyornithines
Schmidt,Meyer,Leitenberger,Stabler,Lieberknecht
, p. 409 - 413 (2007/10/02)
Improved synthetic methods for the preparation of three differently protected (2S,4R)-4-hydroxyornithine (10, 16, 24) have been developed which obviously can be used for the construction of the other stereoisomers. Formation of the corresponding α,β-dideh