16505-91-2Relevant articles and documents
Thioglucose compound and preparation method thereof
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Paragraph 0048-0050; 0063-0065; 0066-0068; 0070; 0074; ..., (2021/09/22)
The invention provides a thioglucose compound which has the following general formula: Wherein R is selected from H or acetyl. The preparation method of the thioglucose compound is easy to obtain, low in production cost and suitable for industrial product
Synthesis of thiosaccharides employing the Pummerer rearrangement of tetrahydrothiopyran oxides
Fujita, Junji,Matsuda, Hiroko,Yamamoto, Kazunori,Morii, Yasuharu,Hashimoto, Masaru,Okuno, Toshikatsu,Hashimoto, Kimiko
, p. 6829 - 6851 (2007/10/03)
The Pummerer rearrangement of 1-deoxy-5-thioglucopyranose derivatives carrying acetonides at the C3,4-positions proceeded regioselectively at the C1 position by treating with TFAA in the presence of pyridine. Studies employing deuterium-labelled derivatives revealed that the reaction was induced by E2 1,2-elimination of trifluoroacetic acid of the trifluoroacetoxy sulfonium intermediate. This methodology was applied to the synthesis of an isomaltotriose derivative consisting of 5-thioglucopyranoside units.
Thio-sugars. I. Radical-promoted thione-thiol rearrangement of cyclic thionocarbonates: Synthesis of 5-thioglucose
Tsuda, Yoshisuke,Sato, Yoshiyuki,Kanemitsu, Kimihiro,Hosoi, Shinzo,Shibayama, Kenji,Nakao, Kayo,Ishikawa, Yuko
, p. 1465 - 1475 (2007/10/03)
The 5,6-O-thiocarbonyl-α-D-glucofuranose derivatives 2, when subjected to one of the following reactions, undergo a radical-promoted thione-thiol rearrangement to yield the 5-S-thiolcarbonates of gluco-configuration 8 as the major product. The reactions are, (A) thermolysis with a catalytic amount of tributyltin hydride and AIBN, (B) photolysis with hexabutyldistannane, and (C) thermolysis with dimethyl phosphonate and benzoyl peroxide. On the other hand, thermolysis of 2 with trialkylsilane (condition D) yielded olefins 13 as the major product. The 5-S-gluco product 8 was converted, in three steps, to 5-thioglucose (21) in 55% yield.