Kinetic acetonation of d-mannose: preparation of 4,6-mono- and 2,3:4,6-di-O-isopropylidene-d-mannopyranose

Gelas, Jacques; Horton, Derek

doi:10.1016/s0008-6215(00)84126-9

Cited by 70 publications

(35 citation statements)

References 16 publications

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“…Acetonation of -mannose under thermodynamic control [52] granted access to furanose 19, whereas kinetic acetonation of -mannose [53] led to pyranose 21. The former was conveniently transformed into furanosyl chloride 22 upon treatment with PPh 3 and CCl 4 in THF at 60°C.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of C‐1 Alkyl and Aryl Glycals from Pyranosyl or Furanosyl Chlorides by Treatment with Organolithium Reagents

et al. 2009

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Section: Resultsmentioning

confidence: 99%

Synthesis of C‐1 Alkyl and Aryl Glycals from Pyranosyl or Furanosyl Chlorides by Treatment with Organolithium Reagents

et al. 2009

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“…The following data belong to pure a-7: (14) À0.08 (14) 0.05 (12 1.2.3. Allyl 2,3:5,6-Di-O-isopropylidene-a-D-mannofuranoside (a-8)…”

Section: Allyl 23:46-di-o-isopropylidene-1-o-a-dmannopyranoside (A-7)mentioning

confidence: 99%

Enantiomerically pure 3-hydroxypropyl diisopropylidene mannose derivatives

Kunig

Lönnecke

Hey‐Hawkins

2011

Carbohydrate Research

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“…The D ‐mannose enyne 42 was prepared from mannose diacetonide ( 45 37) through a synthetic route similar to that used for 20a and 20b (Scheme , a). A sequence consisting of a Wittig reaction, Swern oxidation (no epimerization at C‐4 was observed), stepwise Peterson olefination and dehydrohalogenation then led to the enyne 42 in acceptable overall yield.…”

Section: Resultsmentioning

confidence: 99%

Chemical Synthesis of a Glycolipid Library by a Solid‐Phase Strategy Allows Elucidation of the Structural Specificity of Immunostimulation by Rhamnolipids

Bauer

Brandenburg

Zähringer

et al. 2006

Chemistry A European J

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The first synthesis of a glycolipid library by hydrophobically assisted switching phase (HASP) synthesis is described. HASP synthesis enables flexible switching between solution-phase steps and solid-supported reactions conducted with molecules attached to a hydrophobic silica support. A library of glycolipids derived from the lead compound 1-a strongly immunostimulatory rhamnolipid--with variations in the carbohydrate part, the lipid components, and the stereochemistry of the 3-hydroxy fatty acids was designed and synthesized. The enantioselective synthesis of the 3-hydroxy fatty acid building blocks was achieved by employing asymmetric hydrogenation of 3-oxo fatty acids. Glycolipids were prepared by this approach without any intermediary isolation steps, mostly in excellent yields. Final deprotection to the carboxylic acids was accomplished by enzymatic ester cleavage. All prepared rhamnolipids were tested for their immunostimulatory properties against human monocyte cells by assaying the secretion of the cytokine tumor necrosis factor alpha (TNFalpha) into the medium. The observed structure-activity relationships of rhamnolipids indicate a specific, recognition-based mode of action, with small structural variations in the rhamnolipids resulting in strong effects on the immunostimulatory activities of the rhamnolipids at low micromolar concentrations.

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Kinetic acetonation of d-mannose: preparation of 4,6-mono- and 2,3:4,6-di-O-isopropylidene-d-mannopyranose

Cited by 70 publications

References 16 publications

Synthesis of C‐1 Alkyl and Aryl Glycals from Pyranosyl or Furanosyl Chlorides by Treatment with Organolithium Reagents

Synthesis of C‐1 Alkyl and Aryl Glycals from Pyranosyl or Furanosyl Chlorides by Treatment with Organolithium Reagents

Enantiomerically pure 3-hydroxypropyl diisopropylidene mannose derivatives

Chemical Synthesis of a Glycolipid Library by a Solid‐Phase Strategy Allows Elucidation of the Structural Specificity of Immunostimulation by Rhamnolipids

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