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Journal articles on the topic '3-isopropylidene glycerol'

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Published: 10 December 2022

Last updated: 28 January 2023

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1

Pallavicini, Marco, Cristiano Bolchi, Laura Fumagalli, Ermanno Valoti, and Luigi Villa. "Highly efficient resolutions with isopropylidene glycerol 3-carboxy-2-naphthoate." Tetrahedron: Asymmetry 13, no. 20 (October 2002): 2277–82. http://dx.doi.org/10.1016/s0957-4166(02)00608-0.

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2

Olsson, Henric, and Håkan Bergstrand. "Activation of human neutrophil protein kinase C invitro by 1,2-isopropylidene-3-decanoyl-sn-glycerol (IpOCOC9)." Cellular Signalling 1, no. 4 (January 1989): 405–10. http://dx.doi.org/10.1016/0898-6568(89)90059-4.

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3

Altamura, Emiliano, Arnaud Comte, Alice D’Onofrio, Charlotte Roussillon, Dimitri Fayolle, René Buchet, Fabio Mavelli, Pasquale Stano, Michele Fiore, and Peter Strazewski. "Racemic Phospholipids for Origin of Life Studies." Symmetry 12, no. 7 (July 3, 2020): 1108. http://dx.doi.org/10.3390/sym12071108.

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Although prebiotic condensations of glycerol, phosphate and fatty acids produce phospholipid esters with a racemic backbone, most experimental studies on vesicles intended as protocell models have been carried out by employing commercial enantiopure phospholipids. Current experimental research on realistic protocell models urgently requires racemic phospholipids and efficient synthetic routes for their production. Here we propose three synthetic pathways starting from glycerol or from racemic solketal (α,β-isopropylidene-dl-glycerol) for the gram-scale production (up to 4 g) of racemic phospholipid ester precursors. We describe and compare these synthetic pathways with literature data. Racemic phosphatidylcholines and phosphatidylethanolamines were obtained in good yields and high purity from 1,2-diacylglycerols. Racemic POPC (rac-POPC, (R,S)-1-palmitoyl-2-oleoyl-3-phosphocholine), was used as a model compound for the preparation of giant vesicles (GVs). Confocal laser scanning fluorescence microscopy was used to compare GVs prepared from enantiopure (R)-POPC), racemic POPC (rac-POPC) and a scalemic mixture (scal-POPC) of (R)-POPC enriched with rac-POPC. Vesicle morphology and size distribution were similar among the different (R)-POPC, rac-POPC and scal-POPC, while calcein entrapments in (R)-POPC and in scal-POPC were significantly distinct by about 10%.

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4

Pallavicini, Marco, Ermanno Valoti, Luigi Villa, and Oreste Piccolo. "Reciprocal resolutions between 1-phenylethylamine and carboxyesters of isopropylidene glycerol: improvement of the method by replacing mono-phthalate with 3-carboxy-2-naphthoate." Tetrahedron: Asymmetry 12, no. 17 (September 2001): 2489–95. http://dx.doi.org/10.1016/s0957-4166(01)00439-6.

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5

Bergstrand, Håkan, Britta Lundquist, and Peter Michelsen. "Induction of human basophil histamine release by a novel protein kinase C activator, sn-1,2-isopropylidene-3-decanoyl-glycerol (IpOCOC9): Partial characterization of secretagogue characteristics." European Journal of Haematology 41, no. 5 (April 24, 2009): 467–77. http://dx.doi.org/10.1111/j.1600-0609.1988.tb00229.x.

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6

Pallavicini, Marco, Ermanno Valoti, Luigi Villa, and Oreste Piccolo. "ChemInform Abstract: Reciprocal Resolutions Between 1-Phenylethylamine and Carboxyesters of Isopropylidene Glycerol: Improvement of the Method by Replacing Mono-phthalate with 3-Carboxy-2-naphthoate." ChemInform 33, no. 11 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200211014.

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7

Bergstrand, H., B. Lundquist, and P. Michelsen. "Modulation of human leukocyte histamine release by sn-1,2-isopropylidene-3-decanoyl-glycerol and decanoic acid cyclopentyl methylester in comparison with effects of synthetic diacylglycerols and a phorbol ester." Allergy 44, no. 1 (January 1989): 6–17. http://dx.doi.org/10.1111/j.1398-9995.1989.tb00439.x.

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8

Hashmi, Imran Ali, Holger Feist, Manfred Michalik, Helmut Reinke, and Klaus Peseke. "Dimethylaminomethylene-α-D-xylo-hept-5-ulofuranurononitrile as Building Block in the Synthesis of ‘Reversed’ C-Nucleoside Analogues." Zeitschrift für Naturforschung B 61, no. 3 (March 1, 2006): 292–300. http://dx.doi.org/10.1515/znb-2006-0309.

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Abstract 3-O-Benzyl-6-deoxy-1,2-O-isopropylidene-6-(dimethylaminomethylene)-α-D-xylo-hept-5-ulofuranurononitrile (1) was reacted with amidinium salts, S-methylisothiouronium sulfate, and guanidinium chloride, respectively, in the presence of bases to furnish the 4-(3-O-benzyl-1,2-O-isopropylidene- α-D-xylo-tetrofuranos-4-yl)pyrimidine-5-carbonitriles 2 and the 4-(1,2-O-isopropylidene- α-D-glycero-tetr-3-enofuranos-4-yl)pyrimidine-5-carbonitriles 3, respectively. Treatment of 1 with ethyl 5-aminopyrazole-4-carboxylates yielded the ethyl 7-(3-O-benzyl-1,2-O-isopropylidene- α-D-xylo-tetrofuranos-4-yl)-6-cyanopyrazolo[1,5-a]pyrimidine-3-carboxylates 4 and the ethyl 7-amino-6-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-pentofuranuronoyl)pyrazolo[1,5-a]pyrimidine- 3-carboxylates 5, respectively. Reaction of 1 with 2-benzimidazolylacetonitrile in the presence of sodium methanolate afforded 1-amino-2-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-pentofuranuronoyl) benzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile (6) and 1-amino-2-(3-deoxy-1,2-O-isopropylidene- α-D-glycero-pent-3-enofuranuronoyl)benzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile (7).

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9

Holý, Antonín, Ivan Rosenberg, and Hana Dvořáková. "Synthesis of (3-hydroxy-2-phosphonylmethoxypropyl) derivatives of heterocyclic bases." Collection of Czechoslovak Chemical Communications 54, no. 9 (1989): 2470–501. http://dx.doi.org/10.1135/cccc19892470.

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Analogs of the antiviral 9-(S)-(3-hydroxy-2-phosphonylmethoxypropyl)adenine (HPMPA, I), containing modified heterocyclic base, were prepared from racemic or (S)-N-(2,3-dihydroxypropyl) derivatives II. Compounds II are heated with chloromethylphosphonyl dichloride (XVII), the formed chloromethylphosphonylester chlorides of compounds II react with water to give a mixture of 2'- and 3'-chloromethylphosphonyl derivatives XVIII and XIX, respectively, which on isomerization by boiling with water in the arising acidic medium affords predominantly the 3'-isomer XIX. Treatment of this isomeric mixture with aqueous sodium hydroxide yields a mixture of 2'-O-phosphonylmethyl ethers (predominating, XXI) and 3'-O-phosphonylmethyl ethers of compounds II (XX). This approach has been applied to the synthesis of isomeric mixtures in the racemic as well as in the (S)-series derived from C-2, C-8 and N-6 substituted derivatives of adenine, from hypoxanthine and additional 6-substituted derivatives of purine, from guanine, 3-deazaadenine and other modified purine bases, from uracil, cytosine, their 5-methyl derivatives and 5-fluorouracil. Regioselective synthesis of compounds XXI was performed for biologically active derivatives (derivative of 2-aminoadenine (XXIe), guanine (XXIn), 3-deazaadenine (XXIp) and cytosine (XXIt)) as well as some other compounds (derivative of hypoxanthine (XXIj), uracil (XXIr), thymine (XXIs) and 5-methylcytosine (XXIu)): the former were obtained either from 3'-O-chloromethylphosphonyl derivatives XIX, isolated from the above-mentioned mixtures by ion-exchanger chromatography or HPLC, or by regioselective substitution, whereas the latter compounds were prepared by deamination (compound XXIj from adenine derivative I or the uracil and thymine derivatives XXIr and XXIu from the cytosine derivatives XXIt and XXIu). N-(S)-(3-Hydroxy-2-benzoyloxypropyl) derivative of N4-benzoylcytosine (XXIX) and N2-benzoylguanine (XXIV), obtained from compounds IIn and IIt by successive N-benzoylation, reaction with dimethoxytrityl chloride, benzoylation and mild acid treatment, were subjected to reaction with the chloride XVII and subsequent neutral and alkaline hydrolysis (compound XXIV), or to reaction with sodium methoxide followed by treatment with bromotrimethylsilane (compound XXIX), being thus converted into 1-(S)-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine (XXIt, HPMPC) and 9-(S)-(3-hydroxy-2-phosphonylmethoxypropyl)guanine (XXIn, HPMPG), respectively. The starting compounds (S)-II were synthesized from sodium salt of the corresponding heterocyclic base by reaction with 1-O-p-toluenesulfonyl-2,3-O-isopropylidene-(R)-glycerol (IIIa) (the (RS)-derivatives by reaction with 4-chloromethyl-2,2-dimethyl-1,3-dioxolane (IIIb)), followed by acid hydrolysis.

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10

Moravcová, Jitka, Lucie Špilová, Jindra Čapková, Florence Chery, and Patrick Rollin. "Mitsunobu Transformations of 1,2-O-Isopropylidene-α-D-pentofuranoses Mediated by Zinc Salts." Collection of Czechoslovak Chemical Communications 65, no. 11 (2000): 1745–53. http://dx.doi.org/10.1135/cccc20001745.

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A one-pot regioselective heterofunctionalization of 1,2-O-isopropylidene-α-D-xylofuranose (1) and 1,2-O-isopropylidene-α-D-ribofuranose (2) with zinc azide, zinc thiocyanate or zinc N,N-dimethyldithiocarbamate via the Mitsunobu reaction has been performed. With 2, the reaction gave selectively the desired products substituted at C-5 in good isolated yields (60-65%). However, application of the same reaction conditions to 1 led to the predominant formation of a cyclic 3,5-anhydro derivative. In contrast, the reaction of hydrazoic acid with 1 afforded 5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose besides formerly unknown 5-azido-3,5-dideoxy-1,2-O-isopropylidene-α-D-glycero-pent-3-enofuranose and 3,5-diazido- 3,5-dideoxy-1,2-O-isopropylidene-α-D-ribofuranose; the yields depended on the reaction time and the molar ratio of reagents.

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11

Hemeon, Ivan, and Andrew J. Bennet. "An unexpected elimination product leads to 4-alkyl-4-deoxy-4-epi-sialic acid derivatives." Canadian Journal of Chemistry 86, no. 3 (March 1, 2008): 238–47. http://dx.doi.org/10.1139/v08-006.

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A useful, unexpected β,γ-unsaturated-α-keto ester (ethyl (E)-5-acetamido-3,4,5-trideoxy-6,7:8,9-di-O- isopropylidene-D-manno-non-3-en-2-ulosonate 5) was isolated in 91% yield following ozonolysis and chromatographic purification of its enoate ester precursor ethyl 5-acetamido-2,3,4,5-tetradeoxy-6,7:8,9-di-O-isopropylidene-2-methylene- 4-nitro-D-glycero-D-galacto-nononate (6). When the 4R enoate ester (ethyl 5-acetamido-2,3,4,5-tetradeoxy-6,7:8,9-di-O- isopropylidene-2-methylene-4-nitro-D-glycero-D-talo-nononate, 7) was subjected to the same conditions, enone 5 was a minor product (18%) while the major product did not eliminate HNO2 but instead cyclized to form a five-membered ring containing a hemiaminal linkage between C-2 and the amide nitrogen on C-5 (9, 70%). Conjugate addition to enone 5 opens up the potential to generate 4-substituted sialic acid derivatives, a general route to such compounds that has not been previously reported. In a preliminary investigation of such a route, diethylzinc and dimethylzinc were added to enone 5 resulting in generation of 4-alkyl-substituted cyclic hemiaminal structures 11 and 13, which could be deprotected to form 2,7-anhydrosialic acid analogues 14 and 15. These products could then be converted to peracetylated glycals 16 and 17, the 4-methyl-substituted compound 17 being finally deprotected to give a 4-methyl- substituted analogue of the glycal of sialic acid (5-acetamido-2,6-anhydro-3,4,5-trideoxy-4-methyl-D-glycero-D-talo-non-2-enonic acid 18).Key words: conjugate addition, dialkylzinc reagent, sialic acid, ozonolysis, inhibitors.

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12

Kosma, Paul, Markus Blaukopf, Dmytro Atamanyuk, Nuno Xavier, and Vincent Gerusz. "Synthesis of 1,5-Anhydro-d-glycero-d-gluco-heptitol Derivatives as Potential Inhibitors of Bacterial Heptose Biosynthetic Pathways." Synthesis 49, no. 24 (November 8, 2017): 5320–34. http://dx.doi.org/10.1055/s-0036-1591518.

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A series of 1,5-anhydro-d-glycero-d-gluco-heptitol derivatives have been prepared from 3-O-benzyl-1,2-O-isopropylidene-d-glycero-d-gluco-heptofuranose via conversion into anomeric bromide and thiophenyl derivatives, followed by glycal formation and reductive desulfurization, respectively. Global deprotection of the protected intermediates afforded the 1,5-anhydro derivatives of the d-glycero-d-gluco- and 1,2-dideoxy-d-altro- configuration as well as the 1,5-anhydro-2-deoxy-d-altro-hept-1-enitol. In addition, the 7-O-phosphorylated d-glycero-d-gluco-heptose and its 1,5-anhydro analogue were prepared in good yields utilizing phosphoramidite chemistry. A novel heptitol analogue based on a 1-deoxynojirimycin scaffold was also elaborated via a Wittig-type chain elongation followed by dihydroxylation, separation of the resulting epimers, and global deprotection. The target compounds, however, were not active as inhibitors of the bacterial sedoheptulose-7-phosphate isomerase GmhA.

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13

Jenkinson, S. F., N. Oña, A. Romero, G. W. J. Fleet, A. L. Thompson, and M. S. Pino-González. "6-Azido-3-O-benzyl-6-deoxy-N,N-diethyl-1,2-O-isopropylidene-D-glycero-α-D-gluco-heptofuranuronamide." Acta Crystallographica Section E Structure Reports Online 67, no. 1 (December 4, 2010): o38—o39. http://dx.doi.org/10.1107/s1600536810048944.

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14

Fava, Giovanna Gasparri, Marisa Ferrari Belicchi, Daniele Belletti, Giovanni Casiraghi, and Gloria Rassu. "Crystal and molecular structure of (?)-1,2-O-isopropylidene-3-O-methyl-7,8-dideoxy-?-l-glycero-d-gluco-non-7-enofuranurono-9,6-lactone, C13H18O7." Journal of Crystallographic and Spectroscopic Research 21, no. 3 (June 1991): 261–64. http://dx.doi.org/10.1007/bf01156075.

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15

Ciunik, Z., P. Luger, and K. L. Yu. "Methyl 4,6-O-benzylidene-2-deoxy-2-C-(1,2:3,4-di-O-isopropylidene-L-glycero-D-galacto-hexopyranos-6-yl)-α-D-arabino-hexopyranosid-3-ulose monohydrate." Acta Crystallographica Section C Crystal Structure Communications 48, no. 5 (May 15, 1992): 873–76. http://dx.doi.org/10.1107/s0108270191011897.

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16

Horton, Derek, James P. Roski, and Peter Norris. "Cycloaddition of Cyclopentadiene to 3-Deoxy-1,2:5,6-di-O-isopropylidene-α-d-erythro-hex-3-enofuranose. Synthesis and Representative Chemistry of 1,6-Anhydro-2,3-dideoxy-β-d-glycero-hex-2-enopyran-4-ulose (“Isolevoglucosenone”)." Journal of Organic Chemistry 61, no. 11 (January 1996): 3783–93. http://dx.doi.org/10.1021/jo960032y.

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17

Peters, K., E. M. Peters, J. Raczko, and V. Jäger. "Crystal structure of 3-O-benzy 1-6,8-di-O-benzylidene-5,7-dideoxy-1,2-di-O-isopropylidene-5-nitro-L-glycero-D-galacto-octitol, (C6H5)(C4H6O2)[C3H3(NO2)(0H)(OCH2C6H5)][(C3H3O2)(CH3)2]." Zeitschrift für Kristallographie - New Crystal Structures 214, no. 2 (June 1, 1999): 263–64. http://dx.doi.org/10.1515/ncrs-1999-0257.

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18

Witczak, Zbigniew J., David Lorchak, and Nguyen Nguyen. "A click chemistry approach to glycomimetics: Michael addition of 2,3,4,6-tetra-O-acetyl-1-thio-β-d-glucopyranose to 4-deoxy-1,2-O-isopropylidene-l-glycero-pent-4-enopyranos-3-ulose – a convenient route to novel 4-deoxy-(1→5)-5-C-thiodisaccharides." Carbohydrate Research 342, no. 12-13 (September 2007): 1929–33. http://dx.doi.org/10.1016/j.carres.2007.06.005.

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