67335-77-7Relevant academic research and scientific papers
Convergent de novo synthesis of vineomycinone B2 methyl ester
Chen, Qian,Zhong, Yashan,O'Doherty, George A.
supporting information, p. 6806 - 6808 (2013/07/26)
An efficient de novo synthesis of vineomycinone B2 methyl ester has been achieved. The longest linear route required only 14 steps from achiral commercially available starting materials (4.0% overall yield). The key transformations included the de novo asymmetric synthesis of two key fragments, which were joined by a convergent late stage Suzuki's glycosylation for the construction of the aryl β-C-glycoside. A subsequent BBr3 one-pot debenzylation, demethylation and air oxidation provided vineomycinone B2 methyl ester.
Indium-Mediated Allylation of Aldehydes: A Convenient Route to 2-Deoxy and 2,6-Dideoxy Carbohydrates
Binder, Wolfgang H.,Prenner, Reinhard H.,Schmid, Walther
, p. 749 - 758 (2007/10/02)
The allylation of protected polyhydroxy aldehydes 1 and 14 has been achieved by indium metal with ultrasound promotion generating the diastereomeric pair of homoallylic polyols 3, 4 and 16, 17 respectively with moderate to good stereoselectivity.Pursuing this allylation strategy with the corresponding deprotected polyhydroxy aldehydes led to the same pair of homoallylic polyols but with a quite different ratio of the diastereomers generated.The polyols were further transformed to 2-deoxy (5 and 6) and 2,6-dideoxy (18 and 19) carbohydrates by ozonolysis.
