71049-33-7Relevant academic research and scientific papers
Synthesis of L-Daunosamine
Gurjar, M. K.,Yadav, J. S.,Rama Rao, A. V.
, p. 1139 - 1140 (2007/10/02)
A convenient and inexpensive preparation of methyl 4,6-O-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose (2), an important intermediate for the synthesis of L-daunosamine (1) is described.
Synthetic Application of Iodo- and Bromotrimethylsilane in Saccharide Chemistry
Thiem, Joachim,Meyer, Bernd
, p. 3075 - 3085 (2007/10/02)
In simple model compounds an enhanced rate is observed in the reaction of iodotrimethylsilane with acetates and with cyclohexyl esters.Primary and secondary acetoxy-substituted saccharides show an exclusive formation of glycosyl iodides.Accordingly, pentaacetyl hexopyranoses and iodotrimethylsilane give in high yields the corresponding glycosyl iodides.Methyl glycosides can be transformed similarly, and with lactose octaacetate the formation of α-heptaacetyllactosyl iodide proceeds smoothly without rupture of the interglycosidic linkage.This procedure is particularly valuable for the synthesis of 2-deoxyglycosyl iodides.Corresponding reactions with bromotrimethylsilane are achieved in a similar way.By opening of epoxides with iodotrimethylsilane in the case of sterically fixed saccharide oxiranes the trans-diaxial, and with more flexible derivatives predominantly the trans-diequatorial iodohydrines are obtained.
