669763-26-2Relevant academic research and scientific papers
Synthesis of glycocinnasperimicin D
Nishiyama, Taihei,Kusumoto, Yoshifumi,Okumura, Ken,Hara, Kanako,Kusaba, Shohei,Hirata, Keiko,Kamiya, Yukihiro,Isobe, Minoru,Nakano, Keiji,Kotsuki, Hiyoshizo,Ichikawa, Yoshiyasu
supporting information; experimental part, p. 600 - 610 (2010/05/02)
The first total synthesis of amino sugar antibiotic glycocinnasperimicin D (1) has been achieved by a convergent, three-component coupling strategy. The key steps involve the Heck-Mizoroki reaction by using the iodophenyl glycoside 50 and acryl amide 32 to furnish the right core structure of 1, and the construction of the urea glycoside employing the reaction of glycosyl isocyanate 8 with amino sugar 9. Glycosyl isocyanate 8 was prepared by the oxidation of isonitrile 10, which displayed excellent reactivity in the coupling event. Synthetic roadblocks, encountered during this synthetic effort, have led to the development of the α-selective, Lewis acid catalyzed phenyl glycosylation process with 2-amino-hexopyranose and a procedure for acetonide deprotection without affecting the silyl ethers.
Synthesis of urea-tethered neoglycoconjugates and pseudooligosaccharides in water
Ichikawa, Yoshiyasu,Matsukawa, Yohei,Isobe, Minoru
, p. 3934 - 3938 (2007/10/03)
A novel approach to the synthesis of urea glycosides in aqueous media has been explored. Steyermark's glucopyranosyl oxazolidinone was found to be a good synthon for anchoring glucosyl moieties onto amines and thiols. The present method was successfully a
Urea glycoside synthesis in water
Ichikawa, Yoshiyasu,Matsukawa, Yohei,Isobe, Minoru
, p. 1019 - 1022 (2007/10/03)
A novel approach to the synthesis of urea glycosides in aqueous media has been developed. Reaction of Steyermark's glucosyl carbamate 1 with amines was carried out in water to afford urea glucosides in good yields. This method was successfully applied to
