83470-76-2Relevant academic research and scientific papers
Novel synthesis method of violienamine
-
, (2019/01/16)
The invention provides a novel synthesis method of violienamine. Specifically, the invention provides the novel synthesis method comprising the following steps: carrying out double-bond epoxidation reaction on an intermediate I to obtain an intermediate II; then carrying out rearrangement reaction on the intermediate I to obtain an intermediate III, i.e., violienamine with an amino protection group; removing the protection group from the intermediate II to obtain violienamine.
STEREOSELECTIVE CONVERSION OF VALIENAMINE AND VALIDAMINE INTO VALIOLAMINE
Horii, Satoshi,Fukase, Hiroshi,Kameda, Yukihiko
, p. 185 - 200 (2007/10/02)
Methods are described for the stereoselective conversion of valienamine (2) and validamine (3) into valiolamine (1a), a new pseudo-amino sugar isolated from the fermentation broth of Streptomyces hygroscopicus subsp. limoneus and which is a stronger α-D-glucosidase inhibitor than 2 and 3.Treatment of the acyclic carbamates (4) of 2 with halogenation reagents led to ring closure to afford the halo cyclic carbamates (6), which were reductively dehalogenated and then hydrolyzed to give 1a.Similar treatment of the exomethylene acyclic carbamate (12), derived from 3 via 8-11, resulted in the formation of halo cyclic carbamates (14a,b), which were converted into 1a.The synthesis of epivaliolamine (1b), the C-1 epimer of 1a, starting from 2 and 3, is also described.
