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Synthesis of a higher carbon sugar via directed aldol condensation

✍ Scribed by Slawomir Jarosz; Bert Fraser-Reid

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
264 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-a-D-xylo-hexadialdo-1,4-furanose (2) upon treatment with Lirv(TMS)2 at -500 furnished the e&ate which reacted with methyl 2,3,4-tri-Obenzyl-a-D-glucopyranoside-6-ulose (5) to afford two eythro aldols 3 and 4 in 6:l ratio and 43% yield. 5R;6R Confguration was assigned to the main aldol on the basis of the IH-n.m.r. spectra of appropriate derivatives of 3.

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New convenient and stereoselective route to linear isoprenoids including the construction of Z-trisubstituted double bond is elaborated based on directed aldol condensation. We have previously reported' that the directed aldol condensation2 of dlitbated aldimines J\_ with aldehydes 1 is highly ster