197853-54-6

Upstream product

• 1730-91-2 (S)-2-Methylbutyric acid 
• 197916-21-5 (11S)-11-[[(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(α-L-rhamnopyranosyl)-(1->2)-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoic acid 3_glu-lactone 
• 180782-81-4 (S)-1-(hydroxycarbonyl)pentadec-10-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside 1,3-(B)-lactone 
• 197853-53-5 ethyl O-[2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl]-(1->3)-2,4-di-O-[2(S)-methylbutyryl]-1-thio-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

Total synthesis of tricolorin A

Tricolorin A (1) is a novel tetrasaccharide macrolactone that is a natural herbicide. In this paper is reported a total synthesis of 1. Coupling of hydroxy ester 18 with D-fucosyl trichloroacetimidate 23 gave fucoside 24. Removal of he C-2 pivaloyl group

The First Total Synthesis of Tricolorin A

Keywords: glycosylations; macrocycles; one-pot reactions; total synthesis; tricolorin A

Total synthesis of tricolorin A

Tricolorin A (1), a structurally amazing resin glycoside with promising bioactivities from Ipomoea tricolor cav. (convolvulaceae), was synthesized in a total of 45 steps, with the longest linear sequence of 20 steps and overall yield of 0.65% from D-mannitol. The AB disscharide 19-membered lactone 2 was constructured by a regioselective macrolactonization using Corey-Nicolaou protocol. The macrolactone tetrasaccharide 33 was realized either by 'one- pot two-step' glycosylation procedure or by a stepwise assembly employing the 'armed-disarmed' glycosylation strategy.