192769-54-3Relevant academic research and scientific papers
Anionic ring-opening polymerization of a five-membered cyclic carbonate having a glucopyranoside structure
Azechi, Motohisa,Matsumoto, Kozo,Endo, Takeshi
, p. 1651 - 1655 (2013)
Anionic ring-opening polymerizations of methyl 4,6-O-benzylidene-2,3-O- carbonyl-α-D-glucopyranoside (MBCG) were investigated using various anionic polymerization initiators. Polymerizations of the cyclic carbonate readily proceeded by using highly active initiators such as n-butyllithium, lithium tert-butoxide, sodium tert-butoxide, potassium tert-butoxide, and 1,8-diazabicyclo[5.4.0]undec-7-ene, whereas it did not proceed by using N,N-dimethyl-4-aminopyridine and pyridine as initiators. In a polymerization of MBCG (1.0 M), 99% of MBCG was converted within 30 s to give the corresponding polymer with number-averaged molecular weight (Mn) of 16,000. However, the Mn of the polymer decreased to 7500 when the polymerization time was prolonged to 24 h. It is because a backbiting reaction might occur under the polymerization conditions. Copyright
Thio-sugars III. Radical catalyzed thione-thiol rearrangement of cyclic thionocarbonates on a pyranose ring: Formation of cis-arranged cyclic thiolcarbonates
Tsuda, Yoshisuke,Noguchi, Shinsuke,Kanemitsu, Kimihiro,Sato, Yoshiyuki,Kakimoto, Kyoko,Iwakura, Yumiko,Hosoi, Shinzo
, p. 971 - 980 (2007/10/03)
Pyranoside 3,4-cis-thionocarbonates, under radical-promoted reaction conditions (method A, B, or C, described in the text), gave O-S rearrangement products, 3,4-thiolcarbonates of cis-stereochemistry, in acceptable yields. 2,3-Thionocarbonates of trans-stereochemistry also gave the rearrangement products of cis-stereochemistry preferentially in method B (photolysis with hexabutyldistannane). Although regio-control of the product was not satisfactory in most cases, some of the results suggested that the regioselectivity of the reaction is markedly influenced by the stereochemistry of the anomeric position of the substrates. The products were converted to thioglycosides (peracetate forms) by conventional means.
The Reaction of N-Dichloromethylene-N,N-Dimethylammonium Chloride (Viehe's Salt) with Methyl 4,6-O-Benzylidene-α-D-glucoside. An Alternative Synthesis of Methyl 4,6-O-Benzylidene-α-D-alloside
Copeland, Christopher,Stick, Robert V.
, p. 1031 - 1036 (2007/10/02)
The reaction of methyl 4,6-O-benzylidene-α-D-glucoside with N-dichloromethylene-N,N-dimethylammonium chloride (Viehe's salt) in the presence of a base gives a mixture of carbamates (with triethylamine) or the 2,3-carbonate mainly (with pyridine).The treat
