Abstract
Floridoside (2-O-glycerol-α-D-galactopyranoside) is a natural glycerol glycoside found in red algae and is believed to play important roles in carbon storage, transport, and assimilation and in the regulation of osmotic balance. We describe here a rapid, high-yield, and high-stereoselectivity synthesis of floridoside in which the key step involves the 1,2-cis O-glycosylation of 1,3-dibenzylglycerol with ethyl 2,3,4,6-tetra-O-benzyl-1- thio-β-D-galactopyranoside using iodonium dicollidine perchlorate (IDCP) or N-iodosuccinimide/trimethylsilyl triflate (NIS/TMSOTf) as promoters.
Original language | English |
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Pages (from-to) | 420-427 |
Number of pages | 8 |
Journal | Journal of Carbohydrate Chemistry |
Volume | 27 |
Issue number | 7 |
DOIs | |
State | Published - Sep 2008 |
Externally published | Yes |
Keywords
- 1,2-cis O-glycosylation
- Floridoside
- Glycerol glycoside
- Thioglycoside