172751-32-5Relevant articles and documents
The Miharamycins and Amipurimycin: their Structural Revision and the Total Synthesis of the Latter
Wang, Shengyang,Zhang, Qingju,Zhao, Yachen,Sun, Jiansong,Kang, Wenjia,Wang, Fei,Pan, Haixue,Tang, Gongli,Yu, Biao
supporting information, p. 10558 - 10562 (2019/07/10)
The structural puzzle of amipurimycin, a peptidyl nucleoside antibiotic, is solved by total synthesis and X-ray diffraction analysis, with the originally proposed configurations at C3′ and C8′ inverted and those at C6′, C2′′, and C3′′ corrected. A similar structural revision of the relevant miharamycins is proposed via chemical transformations and then validated by X-ray diffraction analysis. The miharamycins bear an unusual trans-fused dioxabicyclo[4.3.0]nonane sugar scaffold, which was previously assigned as being in the cis configuration.
Synthesis and antiviral evaluation of α-d-2′,3′- didehydro-2′,3′-dideoxy-3′-C-hydroxymethyl nucleosides
Yamada, Kohei,Hayakawa, Hiroyuki,Sakata, Shinji,Ashida, Noriyuki,Yoshimura, Yuichi
scheme or table, p. 6013 - 6016 (2010/11/16)
We have identified a selective SN2′ reaction triggered by iodide ion that leads to the ring-opening of 2,2′-anhydro-α- nucleosides. By applying the method, we have synthesized α-d-2′, 3′-didehydro-2′,3′-dideoxy-3′-C-hydroxymethyl nucleosides, d
Carbohydrate chiral-pool approach to four enantiomerically pure 2-naphthylmethyl 3-hydroxy-2-methylbutanoates
Doboszewski, Bogdan,Herdewijn, Piet
, p. 5551 - 5562 (2008/09/21)
d-Glucose, l-xylose, and d- and l-arabinose were sources of chirality to obtain four enantiomerically pure 3-hydroxy-2-methylbutanoic acids, which were reacted with 2-naphthyldiazomethane to furnish their fluorescent 2-naphthylmethyl esters.
