کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5218922 | 1383341 | 2013 | 10 صفحه PDF | دانلود رایگان |
Here we report a high yielding, stereoselective synthesis of the naturally occurring 1,1â²-disaccharide neotrehalosadiamine (NTD) and some related analogs. Following an eleven-step sequence, seven of which did not require chromatographic separation, NTD was generated in 60% overall yield from the inexpensive, commercially available precursor 1,2:5,6-di-O-isopropylidene-α-d-glucofuranose. The key α,β-linkage of NTD was formed in a highly stereoselective manner by taking advantage of the participating effect of the acyl group at O-2 of the donor glycoside. The influence of electronic effects of disarmed, armed, and superarmed glycosyl donors and acceptors on the outcome of 1,1â²-glycosidation was also observed. Antibacterial studies using NTD and its analogs show detectable but weak anti-staphylococcal activity.
Journal: Tetrahedron - Volume 69, Issue 2, 14 January 2013, Pages 816-825