Hydrosilylation Reaction of Allyl-2,3,4-tri-O-acetyl-β-L- ramnopyranose with methylcyclodisilazane

Author: Natia Demetradze
Keywords: Hydrosilylation Reaction, Farmer rule
Annotation:

Annotation Natia Demetradze “Hydrosilylation Reaction of Allyl-2,3,4-tri-O-acetyl-β-L- ramnopyranose with methylcyclodisilazane” Ivane Javakhishvili Tbilisi State University, I.Chavchavadze av. 3 Silicon compounds play a particularly important role for many living creatures. The silicon compounds perform very important functions in the body of higher animals and human, despite the fact that in most of their organs the content of this element is relatively small. The use of carbohydrates to modify linear and cyclic siloxanes has taken an important place in recent years in both biological and pharmacological studies. incorporation silicon atoms in known drugs may significantly change the nature of the drug, and in some cases give them new properties. By hydrosilylation of 1-0-allyl-2,3,4-tri-O-acetyl-β-L-ramnopyranose (1) with 1,3-bis(dimethyl¬silyl)-2,2,4,4-tetramethylcyclodisilazane (2) in the presence of catalyst – Co2(CO)8, we obtained 1,3-di[3-(2,3,4-tri-O-acetyl-β-L-ramnopyranosyloxy)propyldimethylsilyl]-2,2,4,4-tetramethylcyclodisilazane (3) at the first time. Reactions proceeds according to the following scheme: The reaction mainly occurs according to Farmer rule, although a small amount of Markovnikov addition product is also formed. By deacetylation of compounds 4 in absolute methanol in the presence of sodium methoxide, we obtained 1,3-di[3-(β-L-ramnopyranosyloxy)propyldimethylsilyl]-2,2,4,4-tetrame¬thylcyclodisilazane (4). The structure of obtained compounds was established by physical-chemical methods of analysis. With the purpose of theoretical substantiation of the direction of the hydrosilylation reactions of 1-0-allyl-2,3,4-tri-O-acetyl-β-L-ramnopyranose (1), quantum-chemical calculations were carried out using the semi-empirical AM1 method.

Lecture files:

ალილ–2,3,4–ტრი–O-აცეტილ–,L-რამნოპირანოზის მეთილციკლოდისილაზანთან ჰიდროსილილირების რეაქცია [ka]