959409-99-5Relevant academic research and scientific papers
Method for preparing calystegine and intermediate thereof
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Paragraph 0168; 0169; 0170, (2016/10/10)
The invention relates to the field of the synthesis of natural products, and discloses a method for preparing calystegine and an intermediate thereof. The calystegine has a structure as shown in a formula I. The method comprises the following steps of, in the presence of a protecting agent, carrying out a protective reaction on a hydroxyl group in primary alcohol as shown in a formula II; enabling alkene as shown in a formula III to react with ozone; carrying out an ylide reaction on aldehyde as shown in a formula IV; carrying out a deprotection reaction on alkenyl iodine as shown in a formula V; enabling alcohol as shown in a formula VI to react with a first oxidizing agent; carrying out an NHK (Nozaki-Hiyama-Kishi) reaction on aldehyde as shown in a formula VII; enabling alcohol as shown in a formula VIII to react with a second oxidizing agent; carrying out a reducing reduction on an unsaturated ketone as shown in a formula IX. By using the method, the calystegine is efficiently synthesized with a succinct route through raw materials which are easily obtained and are further low-cost. Through the method, a new route is provided for the synthesis of calystegine-series compounds, and a firm foundation is provided for screening a compound with a biological activity and a medicinal value. The formula I is shown in the description.
D-Glucosamine trimethylene dithioacetal derivatives: Formation of six- and seven-membered ring amino carbasugars. Synthesis of (-)-calystegine B 3
Chen, Yue-Lei,Redlich, Hartmut,Bergander, Klaus,Froehlich, Roland
, p. 3330 - 3339 (2008/09/21)
By virtue of carefully chosen protecting groups, d-glucosamine trimethylene dithioacetal derivatives were successfully oxidized to the corresponding 6-aldehydes. This methodology reverses the donor and acceptor position on a normal open chain sugar and changes the relative position of the N-substituent. From the 6-aldehydes, heptose epoxide derivatives were prepared by a Corey-Chaykovsky reaction, and cyclized by the Corey-Seebach method. Depending on the designed protecting groups, the orthogonally protected six- and seven-membered ring amino carbasugars can be produced selectively and efficiently. (-)-Calystegine B3 was synthesized from one of those products with high yield. This is the first anionic cyclization pathway to calystegine type structures. This journal is The Royal Society of Chemistry.
