18685-18-2

Usage

Chemical Properties

Light Yellow Oil

Uses

A derivative of glucofuranose.

InChI:InChI=1/C19H26O6/c1-18(2)21-11-13(23-18)14-15(20-10-12-8-6-5-7-9-12)16-17(22-14)25-19(3,4)24-16/h5-9,13-17H,10-11H2,1-4H3

Upstream product

• 100-44-7 benzyl chloride 
• 64656-76-4 Natrium-Verbindung der O¹,O²;O⁵,O⁶-Diisopropyliden-α-D-glucofuranose 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 16713-80-7 3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 
• 50-99-7 D-glucose 
• 99605-27-3 3-O-(tert-butyldimethylsilyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 611-74-5 N,N-dimethylbenzamide 
• 77-76-9 2,2-dimethoxy-propane 
• 65434-49-3 3-O-benzyl-1,2-O-isopropylidene-α-D-galactofuranose 
• 4205-23-6 D-gulose 
• 2397-26-4 N,N-dimethyl(chlorophenylmethylene)ammonium chloride 
• 13964-22-2 3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 10230-17-8 O³-benzyl-D-glucose 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 18006-25-2 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose diacetate 
• 23313-05-5 6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose 
• 23313-03-3 (R)-2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl 4-methylbenzenesulfonate 
• 477329-91-2 Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-azidomethyl-4-benzyloxy-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-tetrahydro-pyran-3-yl ester 
• 628281-00-5 allyl (methyl 2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 628281-04-9 allyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 628280-99-9 allyl (methyl 2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 628281-02-7 allyl (methyl 3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 628281-03-8 allyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 628281-01-6 allyl (methyl 3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 93382-47-9 methyl (acetyl 2,4-di-O-acetyl-3-O-benzyl-α,β-L-idopyranoside)uronate 
• 87326-78-1 methyl 3-O-benzyl-β-L-idopyranuronate 

Relevant academic research and scientific papers

Chemo-enzymatic route to bridged homolyxofuranosyl-pyrimidines

Synthesis of 2′-O,5′-C-bridged-β-D-homolyxofuranosyl nucleosides U and T have been achieved starting from diacetone-D-glucose in overall yields 55.7 and 57.1%, respectively. Quantitative regioselective monoacetylation of the lone primary hydroxyl group in

A carbohydrate-based approach for the total synthesis of (-)-dinemasone B, (+)-4a-epi-dinemasone B, (-)-7-epi-dinemasone B, and (+)-4a,7-di-epi-dinemasone B

(-)-Dinemasone B was isolated by Krohn and co-workers from a culture of the endophytic fungus Dinemasporium strigosum and has shown promising antimicrobial activity. Described herein is the first total synthesis of (-)-dinemasone B, (+)-4a-epi-dinemasone B, (-)-7-epi-dinemasone B, and (+)-4a,7-di-epi-dinemasone B. Their absolute configurations were also determined. The developed synthesis features a stereoselective reduction of C-glycosidic ketone, lactonization, and E-olefination of aldehyde starting from d-glucose.

An improved method for the preparation of 3-O-benzyl-6-O-pivaloyl-α-D-glucopyranose 1,2,4-orthopivalate

The synthetic route to 3-O-benzyl-6-O-pivaloyl-α-D-glucopyranose 1,2,4-orthopivalate (1), which was previously established, was shortened by introducing two novel reactions, regioselective pivaloylation with dibutyltin oxide in toluene for the regioselective activation of hydroxyl groups, and intramolecular orthoesterification with benzenesulfonyl chloride and triethylamine in dichloromethane. Compound 1 was obtained in 58.8% overall yield from commercially available 1,2:5,6-di-O-isopropylidene-α-D-glucopyranose (2) via four reaction steps.

Syntheses and complexing ability of α-d-gluco- and α-d-xylofuranoside-based lariat ethers

Chiral monoaza-15-crown-5 lariat ethers attached to a 1,2-O-isopropylidene-α-d-glucofuranoside unit (10–13), monoaza-16-crown-5 lariat ethers fused to 1,2-O-isopropylidene-α-d-glucofuranoside- (18) and to 1,2-O-isopropylidene-α-d-xylofuranoside units (23 and 24) have been synthesized. The alkali metal- and ammonium picrate extracting ability of these macrocycles was investigated in dichloromethane–water system. In general, the 15-membered macrocycles (10–13) showed, for almost all cations, a more considerable extracting ability, than the 16-membered lariat ethers (18, 23 and 24). Plasticized PVC membrane electrodes (ISEs) were prepared from the α-d-glucofuranoside-based triphenylmetyl (trityl) ether derivative (18), and its potentiometric selectivities and complex formation constants were determined with the segmented sandwich membrane method. Furthermore, the binding affinities of ionophores to different metal ions were also measured by competitive ESI–MS experiments. One of the 1,2-O-isopropylidene-α-d-glucofuranoside-based lariat ethers (13) exhibited a high selectivity for silver ion (Ag+).

Synthesis and antimicrobial activity of (?)-cleistenolide and analogues

Using the “chiral pool” approach, two modified total syntheses of the biologically active δ-lactone cleistenolide (1) have been achieved starting from D-glucose. These approaches also enabled the preparation of novel analogues and derivatives of natural product 1. The applied strategy for the synthesis of 1 involves: the initial degradation of the chiral precursor for a single C-atom, C2-fragment chain extension using Z-selective Wittig reaction, and the final δ-lactonization. All tested cleistenolide analogues displayed antimicrobial activity against a panel of nine microbial strains, most of them superseding the activity of cleistenolide itself, and, in some cases, coming close in value to the observed minimal inhibitory concentrations of chloramphenicol. Increased lipophilicity of the derivatives and the non-sterically congested conjugated lactone moiety were a prerequisite for analogues with high inhibitory activity against S. aureus and, in general, Gram-positive bacteria.

Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups

The cleavage of benzyl ethers by catalytic hydrogenolysis or Birch reduction suffers from poor functional group compatibility and limits their use as a protecting group. The visible-light-mediated debenzylation disclosed here renders benzyl ethers temporary protective groups, enabling new orthogonal protection strategies. Using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a stoichiometric or catalytic photooxidant, benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time can be reduced from hours to minutes in continuous flow.

Gram-level total synthesis method of sulfur onium salt type natural product neoponkoranol extracted from salacia plants

The invention belongs to the field of chemical synthesis and particularly relates to a gram-level total synthesis method of a sulfur onium salt type natural product neoponkoranol with hypoglycemic activity extracted from salacia plants. According to the m

Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands

Glycosyl triazoles are conveniently accessible and contain multiple metal-binding units that may assist in metal-mediated catalysis. Azide derivatives of d-glucose have been converted to their respective aryltriazoles and screened as ligands for the synthesis of 2-substituted benz-fused azoles and benzimidazoquinazolinones by Cu-catalyzed intramolecular Ullmann type C-heteroatom coupling. Good to excellent yields for a variety of benz-fused heterocyles were obtained for this readily accessible catalytic system.

ACIDIC DYSTROGLYCAN OLIGOSACCHARIDE COMPOUND AND METHOD FOR MAKING SAME

A synthetic dystroglycan oligosaccharide comprising Formula (I) wherein a repeating disaccharide motif consists of Glucuronic Acid (ClcA) and Xylose (Xyl) having a defined glycosyl connection GlcA-β-(1→3)-Xyl-α-(1→3)-GlcA; wherein either end of the synthetic dystroglycan oligosaccharide is conjugatable with chemical or biological vehicle or support; wherein the non-reducing terminal (II) is conjugatable with any oligosaccharides or groups that can modify a hydroxyl functionality; and wherein the reducing terminal is conjugatable with any tags, oligosaccharides or anything that can modify a hydroxyl functionality.

Total synthesis of viscumneoside III of Viscum coloratum

The first total synthesis of viscumneoside III, a promising anti-angina pectoris dihydroflavone O-glycoside isolated from Viscum coloratum was described here. Trichloroaceti-midate was employed as the apiofuranosyl donor to construct the key building block of homoeriodictyol-7-O-β-D-apiosyl-(1 → 2)-β-D-glycoside (1). The longest linear sequence (from 2 to 1) in the synthetic route required thirteen steps and afforded the final product 1 with an overall yield of 6.3%.