Direct preparation of 2-deoxy-D-glucopyranosides from glucals without Ferrier rearrangement

Bolitt, Véronique; Mioskowski, Charles; Lee, S. G.; Falck, John R.

doi:10.1021/jo00310a006

Cited by 221 publications

(108 citation statements)

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“…[50] Starting from l-rhodinal benzyl ether (5 b) glycosylation with precursor 6 gave the desired glycoside 20. Different glycosylation procedures were tested: with triphenyl phosphonium bromide [51] the required precursor was obtained, but only as a mixture of epimers and in extremely poor yield. Thiems iodoglycosylation method [9,52] was tested next.…”

Section: Resultsmentioning

confidence: 99%

The Tandem Ring‐Closing Metathesis–Isomerization Approach to 6‐Deoxyglycals

Schmidt

Biernat

2008

Chemistry A European J

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Protected 3,6-dideoxyglycals have been synthesized de novo as single isomers starting from ethyl lactate by using the tandem RCM-isomerization reaction as the key step. Different relative configurations become accessible by addition of vinyl- or allyl-metal compounds to protected lactaldehydes under Cram-chelate or Felkin-Anh control. The concept is exemplified for glycals of L-rhodinose and L-amicetose, as well as for ring-expanded non-natural analogues thereof. This novel approach to glycals is also applicable to the synthesis of disaccharide glycals via a reiterative strategy, as exemplified for the dimer of L-rhodinose and its non-natural ring expanded analogue.

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Section: Resultsmentioning

confidence: 99%

The Tandem Ring‐Closing Metathesis–Isomerization Approach to 6‐Deoxyglycals

Schmidt

Biernat

2008

Chemistry A European J

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“…[28] Glycosylation methodology is outlined in Scheme 1 for the preparation of 4-O-(3,4-di-O-benzyl-2-deoxy-a-l-fucosyl)-3-O-benzyl-2-deoxy-a-lrhamnose 25. Addition of p-methoxybenzyl alcohol [29] to the easily available 3,4-di-O-acetyl-l-fucal 14, [30] followed by deacetylation with sodium methoxide, gave the p-methoxybenzyl fucoside 15. Alkylation with excess benzyl chloride and potassium hydroxide as the base afforded p-methoxybenzyl-3,4-di-Obenzyl-2-deoxyfucoside 16.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Evaluation, and Molecular Modeling Studies of Rebeccamycin Analogues Modified in the Carbohydrate Moiety

et al. 2008

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A new series of indolocarbazole glycosides containing disaccharides were synthesized and their in vitro antiproliferative activity was evaluated against three human cancer cell lines (A2780, H460, and GLC4). Cytotoxicity appeared to be remarkably affected by the regio- and stereochemical features of the disaccharide moiety. In vivo antitumor activity of the compounds studied, two of which having IC(50)<100 nm, was determined using ovarian cancer cell line A2780 xenografted on nude mice. One compound showed an efficacy similar to that of the reference compound edotecarin, though with a lower long-lasting activity. The topoisomerase I inhibitory properties of some compounds were also examined. Molecular dynamics simulations of the ternary topoisomerase I-DNA-ligand complexes were performed to analyze the structural features of topoisomerase I poisoning with this class of indolocarbazoles. A plausible explanation of their biological behavior was provided. These theoretical results were compared with the recently published crystal structure of an indolocarbazole monosaccharide bound to the covalent human topoisomerase I-DNA complex.

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“…Recently, Falck and co-workers reported on the unique ability of triphenylphosphine hydrobromide (TPHB) to promote the addition of oxygen nucleophiles to glucals to give the corresponding acetals without the double bond rearrangement (Ferrier reaction) (17). On the basis of this report, we became interested in using TPHB for the ethanolysis of aucubin.…”

Section: Chemical Synthesismentioning

confidence: 99%