1986
DOI: 10.1016/s0040-4020(01)90570-8
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On the communication of chirality from furanose and pyranose rings to monosaccharide side chains: anomalous results in the glucose series

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Cited by 94 publications
(25 citation statements)
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“…Compounds 13 and 15 were obtained (Scheme 2) by Dess Martin oxidation of methyl 6- O -benzyl-2,3-di- O -methyl-α-D-glucopyranoside 50 74 to the corresponding ketone 51 followed by treatment with allylmagnesium chloride in THF at 0 °C when the 4- C -allyl galacto and 4- C -allyl-glucopyranosides 52 and 53 were obtained in 60 and 22% yield, respectively. Etherification with sodium hydride and methyl iodide then gave the ethers 54 and 55 , which were subjected to ozonolysis with reductive work up to give the 4- C -(2-hydroxyethyl) derivatives 56 and 57 in good yield.…”
Section: Resultsmentioning
confidence: 99%
“…Compounds 13 and 15 were obtained (Scheme 2) by Dess Martin oxidation of methyl 6- O -benzyl-2,3-di- O -methyl-α-D-glucopyranoside 50 74 to the corresponding ketone 51 followed by treatment with allylmagnesium chloride in THF at 0 °C when the 4- C -allyl galacto and 4- C -allyl-glucopyranosides 52 and 53 were obtained in 60 and 22% yield, respectively. Etherification with sodium hydride and methyl iodide then gave the ethers 54 and 55 , which were subjected to ozonolysis with reductive work up to give the 4- C -(2-hydroxyethyl) derivatives 56 and 57 in good yield.…”
Section: Resultsmentioning
confidence: 99%
“…To assess whether the metalated hopane had been formed, we used aldehydes 17, [31] 18, [32] and 19, 1 derived from d-ribose (Scheme 1), for the cross-coupling reactions. Unfortunately though, classical Grignard or Barbier halogen/metal exchanges with Mg, Zn, or Li failed to give the desired hopanyl-metal species from iodohopane 15 or bromohopane 16, which could be easily prepared from known hopanol 13 (Scheme 1).…”
Section: Generation Of Hopanyllithiummentioning
confidence: 99%
“…After this time the dark blue color of the reaction mixture remained unchanged. The mixture was stirred at À78 8C for 3 min, and a solution of aldehyde 17 [31] (220.0 mg, 1.1 mmol) in anhydrous THF (1 mL) was then added dropwise at À78 8C over a period of 5 min. After stirring at À78 8C for 10 min, the reaction mixture was allowed to warm up gradually to room temperature and stirring was continued overnight.…”
Section: -Hydroxy-ribosylhopane (20)mentioning
confidence: 99%
“…5g,i Our approach to addressing that challenge (bottom of Scheme 1) has been to use a tetrahydrofuran substrate (8 and 9) containing an exocyclic alkene. 6 When activated by a powerful bromenium source such as BDSB (10, Et 2 SBr$SbCl 5 Br), 7 an oxonium intermediate (11 and 12) is produced which subsequently undergoes ring-opening either by elimination of the neighboring silane or nucleophilic attack by the Boc-protected alcohol to afford an 8membered ring containing either an alkene (13) or protected diol (14), respectively. To date, we have synthesized natural products 1-6, among others, concisely through this approach due to the ease of varying the chiral information encoded into the starting substrates.…”
Section: Introductionmentioning
confidence: 99%