87219-80-5Relevant articles and documents
Stereoselective synthesis of 2-alkynyl and 2-alkenyl-1-ethoxy glucosides - new types of acetal-glycosides for use in the treatment of cancer
Tietze, Lutz F.,Fischer-Beller Anja
, p. 169 - 182 (1994)
Reaction of propargylaldehyde diethyl acetals 1, 2, 3, and 4 and 2,3,4,6-tetra-O-acetyl-1-O-trimethylsilyl-β-D-glucopyranose 5a in the presence of catalytic amounts of trimethylsilyl trifluoromethanesulfonate at -78 deg C gives the acetylated acetal-β-glucosides 6-9 in 60-90percent yield with retention of configuration at C-1.Likewise 2,3,4,6-tetra-O-acetyl-1-O-trimethylsilyl-β-D-glucopyranose 5a afforded, after in situ anomerisation to 5b with 4, the corresponding acetal-α-glucoside 10.Hydrogenation and subsequent deprotection yielded the highly acid-sensitive 2-alkenyl-1-ethoxy glucosides which are of interest as selective anticancer agents.
A novel utilization of trifluoromethanide as a base: A convenient synthesis of trimethylsilylacetylene
Yoshimatsu, Mitsuhiro,Kuribayashi, Masako
, p. 1256 - 1257 (2007/10/03)
Trimethysilylation of trimethylsilylacetylene was performed using trifluoromethanide as a base. Trifluoromethanide reacted with terminal acetylene and acetylenic selenides as a base or a nucleophile to give trimethylsilylacetylenes in high yields. Results indicated that the phenylseleno group effectively stabilized the intermediate vinyl anion that went through the cyclization reaction.
A new method of synthesis for propargylic amines and ethers via benzotriazole derivatives using sodium dialkynyldiethylaluminates
Ahn, Jin Hee,Joung, Meyoung J.,Yoon, Nung Min,Oniciu, Daniela C.,Katritzky, Alan R.
, p. 488 - 492 (2007/10/03)
1-(α-Aminoalkyl)benzotriazoles react with sodium dialkynyldiethylaluminates to give propargylic amines in excellent yields, including unsubstituted N,N-dialkyl propargylamines, which are difficult to obtain from lithium acetylide. The reaction of α-benzotriazolyl alkyl ethers and sodium dialkynyldiethylaluminate in the presence of zinc iodide also gives propargylic ethers in excellent yields. Unsubstituted propargyl ethers are prepared via the desilylation of trimethylsilylpropargyl ethers.
Substitution of the acetoxy groups of dialkoxymethylacetates by organometallic reagents: a route to allyl-, propargyl-, homoallyl-, homopropargyl- and α-stannylacetals
Beaudet, Isabelle,Duchene, Alain,Parrain, Jean-Luc,Quintard, Jean-Paul
, p. 201 - 212 (2007/10/02)
The substitution of the acetoxy groups of dialkoxymethylacetates by organometallic reagents has been examined in a search for new methods of preparing functional acetals.The efficiency of the substitution of the acetoxy group is highly dependent on the nature of the organometallic reagents: soft nucleophiles with strong electrophilic assistance by the counterion are the best reagents.Allyl-, propargyl-, homoallyl-, homopropargyl- and α-stannylacetals have been made by this route, in which dialkoxymethylacetates often function as useful substitutes for dialkylphenylorthoformates.
