Enantiomerically pure 3-hydroxypropyl diisopropylidene mannose derivatives

Kunig, Johannes; Lönnecke, Peter; Hey‐Hawkins, Evamarie

doi:10.1016/j.carres.2011.03.035

Cited by 6 publications

(4 citation statements)

References 35 publications

(15 reference statements)

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“…The crude material was purified via column chromatography using 3:7 EtOAc/hexane to yield 13 as a mixture of anomers (18.00 g, 54% over 2 steps). NMR spectra for 13 matched those previously reported in the literature. , …”

Section: Methodssupporting

confidence: 73%

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Synthesis of a Diacetonide-Protected, Mannose-Based Oxepine: Configurational Control of Anomeric Acetate Activation

Pero

Peczuh

2022

J. Org. Chem.

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Carbohydrate-based oxepines are seven-membered-ring oxacycles containing an enol ether moiety. These compounds have been used as intermediates in the preparation of septanose carbohydrates by functionalization through their double bond. Reported here is a new synthesis of a carbohydrate based oxepine that uses 2,3;4,6-di-O-acetonide mannose as a key starting material. The oxepine is an important precursor used in the synthesis of septanose glycomimetics of mannopyranosides. The central feature of the synthesis is a two-step sequence that converts a septanose 1,2-di-O-acetate to the septanosyl bromide and onward to the oxepine via a reductive elimination.

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Section: Methodssupporting

confidence: 73%

“…NMR spectra for 13 matched those previously reported in the literature. 33,34 2,3:4,6-Di-O-isopropylidene α-Mannose (5). Into a 100 mL round-bottom flask were added allyl-2,3:4,6-di-O-isopropylidene mannose (13) (1.30 g, 4.33 mmol, 1 equiv) and 24 mL of Et 2 O.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis of a Diacetonide-Protected, Mannose-Based Oxepine: Configurational Control of Anomeric Acetate Activation

Pero

Peczuh

2022

J. Org. Chem.

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“…Analytical data were in accordance with literature. [48] 1 Method 1: Pursuant to general procedure GP4, 2.60 g (10.00 mmol) 2, 2.00 g (50.00 mmol) sodium hydroxide (50% in water), and 15.36 g (40.00 mmol) 1,3-bis(p-toluenesulfonyl)-propane (28) and chromatographic purification (toluene/acetone 25:1) on silica gel gave 36 (0.70 g, 15%) as colorless oil.…”

Section: -O-allyl-23:56-di-o-isopropylidene-α-d-mannofuranose (25)mentioning

confidence: 97%

Synthesis of Glycoconjugated Phthalonitriles for New Phthalocyanine-Based Photosensitizers

Crucius

Hanack

Ziegler

2015

Journal of Carbohydrate Chemistry

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Excellent photophysical and photochemical properties completed by magnificent takeup rates in malignant tissues attracted a great deal of interest to the application of glycosylated and glycoconjugated phthalocyanines in photodynamic therapy. In this study we describe the concise synthesis and full characterization of 16 differently 3,6-bisglycoconjugated phthalonitriles 3, 5, 6, 8, and 48-59, which are precursors for a new generation of photosensitizers, namely, nonperipheral glycoconjugated phthalocyanines. The first example for the synthesis of a nonperipheral glycoconjugated zinc phthalocyanine 60 from phthalonitrile 48 is also presented in this work.

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“…We are, therefore, now focusing on different glycosides, such as mannose [34], and different connectivities with the phosphorus atom, e.g., via the anomeric position, to achieve higher selectivity.…”

Section: Carbaboranyl Glycophosphonatesmentioning

confidence: 99%

Imitation and modification of bioactive lead structures via integration of boron clusters

Stadlbauer

Frank

Scholz

et al. 2012

Pure and Applied Chemistry

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In medicinal chemistry, carbaboranes can be employed either as boron carriers for boron neutron capture therapy (BNCT) or as scaffolds for radiodiagnostic or therapeutic agents. We have developed a suitable synthesis employing the phosphoramidite method to connect meta-carbaboranyl bis-phosphonites with the 6'-OH group of isopropylidene-protected galactose, followed by oxidation or sulfurization to give the corresponding bis-phosphonates. Deprotection yielded water-soluble compounds. The corresponding disodium salts exhibit especially low cytotoxicity. Preliminary results on the in vivo toxicity and biodistribution of two compounds in mice indicated a lack of selectivity for the cotton rat lung (CRL) tumor chosen for the experiment. For the incorporation of carbaboranes into breast tumorselective modified neuropeptide Y, [F 7 , P 34 ]-NPY, a synthesis of a carbaborane-modified lysine derivative was developed. Linkage of the lysine to the boron cluster was achieved by using a propionic acid spacer. Incorporation of the amino acid derivatives into NPY and [F 7 , P 34 ]-NPY by solid-phase peptide synthesis was successful. Preliminary studies showed that the receptor binding affinity and signal transduction of the boron-modified peptides were very well retained.Asborin, the carbaborane analogue of aspirin, is a rather weak inhibitor of cyclooxygenase-1 (COX-1) and COX-2, but a highly potent aldo/keto reductase 1A1 (AKR1A1) inhibitor. Modification either at the carboxyl group or at the chlorophenyl ring in indomethacin with ortho-and meta-carbaboranyl derivatives gave active derivatives only for the ortho-carbaborane directly attached to the carboxyl group, while the corresponding adamantyl and meta-carbaboranyl derivatives were inactive.

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Enantiomerically pure 3-hydroxypropyl diisopropylidene mannose derivatives

Cited by 6 publications

References 35 publications

Synthesis of a Diacetonide-Protected, Mannose-Based Oxepine: Configurational Control of Anomeric Acetate Activation

Synthesis of a Diacetonide-Protected, Mannose-Based Oxepine: Configurational Control of Anomeric Acetate Activation

Synthesis of Glycoconjugated Phthalonitriles for New Phthalocyanine-Based Photosensitizers

Imitation and modification of bioactive lead structures via integration of boron clusters

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