20316-77-2

Usage

Uses

Used in Pharmaceutical Industry:
(3R,4S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,7-dimethyl-4-prop-2-enoxy-2,6,8-trioxabicyclo[3.3.0]octane is used as a potential pharmaceutical compound for its unique chemical structure and properties. Its tricyclic ether nature and the presence of functional groups such as prop-2-enoxy and methyl groups may contribute to its potential therapeutic applications.
Used in Materials Science:
(3R,4S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,7-dimethyl-4-prop-2-enoxy-2,6,8-trioxabicyclo[3.3.0]octane is used as a component in the development of new materials with specific properties. Its complex structure and functional groups may enable the creation of materials with unique characteristics, such as improved stability, reactivity, or selectivity, for various applications in materials science.

InChI:InChI=1/C15H24O6/c1-6-7-16-11-10(9-8-17-14(2,3)19-9)18-13-12(11)20-15(4,5)21-13/h6,9-13H,1,7-8H2,2-5H3/t9-,10-,11+,12?,13?/m1/s1

Upstream product

• 64656-76-4 Natrium-Verbindung der O¹,O²;O⁵,O⁶-Diisopropyliden-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 106-95-6 allyl bromide 
• 16713-80-7 3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 
• 107-05-1 3-chloroprop-1-ene 
• 753488-63-0 1,2:5,6-di-O-isopropylidene-3-O-methylprenyl-α-D-glucofuranose 
• 50-99-7 D-glucose 
• 109-64-8 1,3-dibromo-propane 
• 582-52-5 1,2:5,6-diacetone-D-glucose 
• 492-62-6 alpha-D-glucopyranose 
• 556-56-9 allyl iodid 
• 109-70-6 1.3-chlorobromopropane 
• 142363-22-2 1,2:5,6-di-O-isopropylidene-3-O-(allenyl)-α-D-glucofuranoside 
• 99605-27-3 3-O-(tert-butyldimethylsilyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 40690-74-2 1,2:5,6-di-O-isopropylidene-3-O-acrylate-α-D-glucopentoaldo-1,4-furanose 
• 39698-00-5 acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside 
• 502181-48-8 phenyl 3-O-allyl-2,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside 
• 502181-50-2 phenyl 2,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside 
• 502181-52-4 phenyl 3-O-acetyl-2,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside 
• 502181-38-6 phenyl 3-O-allyl-2,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside 
• 502181-59-1 methyl (2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside 
• 502181-63-7 methyl 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside 
• 134311-68-5 C₁₈H₂₄O₅ 
• 134311-67-4 C₂₁H₂₈O₅ 
• 134311-69-6 C₂₀H₂₆O₆ 
• 127874-89-9 3-O-acetyl-2,4-di-O-benzyl-6-deoxy-D-glucopyranose 
• 134311-58-3 3-O-Acetyl-2,4-di-O-benzyl-6-deoxy-α-D-glucopyranosyl chloride 
• 134311-73-2 C₄₉H₇₀O₆ 

Relevant academic research and scientific papers

Synthesis and characterization of a new methacrylic glycomonomer

The carbohydrate containing monomer 3-O-(2′-hydroxy-3′- methacryloyloxypropyl)-1,2: 5,6-di-O-isopropylidene-α-D-glucofuranose was easily prepared from D-glucose and methacrylic acid in 4 steps. The structure of the new methacrylic monomer was confirmed using FTIR, NMR (including 1H-NMR, 13C-NMR, COSY, HMQC and HMBC), and HPLC-MS. This work is part of our groups effort to obtain new polymers based on renewable resources with enhanced biodegradability and biocompatibility.

Efficient metathesis route to the B-ring of eleutherobin and other medium-sized cyclic ethers

A short and efficient RCM route is reported for the synthesis of the B-ring of eleutherobin and other medium-sized cyclic ethers from readily available 1,2,5,6-diisopropylidene-d-glucose. This strategy is successfully extended to the synthesis of a few bicyclic ethers, which may find applications in the synthesis of novel bicyclic nucleosides.

A ring-closing metathesis approach to a synthesis of the B ring of eleutherobin

A short and efficient RCM route is reported for the construction of the key nine-membered B ring of eleutherobin starting from the readily available 1,2,5,6-diisopropylidene-D-glucose.

Stereoselective synthesis of chiral oxepanes and pyrans through intramolecular nitrone cycloaddition in organized aqueous media

A highly stereoselective surfactant-catalyzed intramolecular nitrone (formed by dehydration in water) cycloaddition in aqueous media leading to exclusive formation of a single isomer is reported. Either oxepane or pyran is formed from 3-O-allyl furanoside

An eco-compatible strategy for the diversity-oriented synthesis of macrocycles exploiting carbohydrate-derived building blocks

An efficient, eco-compatible diversity-oriented synthesis (DOS) approach for the generation of library of sugar embedded macrocyclic compounds with various ring size containing 1,2,3-triazole has been developed. This concise strategy involves the iterative use of readily available sugar-derived alkyne/azide-alkene building blocks coupled through copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction followed by pairing of the linear cyclo-adduct using greener reaction conditions. The eco-compatibility, mild reaction conditions, greener solvents, easy purification and avoidance of hazards and toxic solvents are advantages of this protocol to access this important structural class. The diversity of the macrocycles synthesized (in total we have synthesized 13 macrocycles) using a set of standard reaction protocols demonstrate the potential of the new eco-compatible approach for the macrocyclic library generation.

Chiron approach to formal synthesis of 8,9-dideoxyneodysiherbaine (MSVIII-19)

Background: The synthesis of biologically active model compounds represents a valuable tool for medicinal chemistry. In this regard, the synthesis of MSVII-19, a structurally simplified model compound of Dysiherbaine, developed by the group of Sasaki, was synthesized with the intention of preparing a powerful agonist or antagonist of glutamate receptor. Therefore, the synthesis of an advanced intermediate in the Sasaki's synthesis of MSVIII-19 is reported. Methods: Taking advantage of the furanose ring of the diacetone-D-glucose (DAG), the cis-fused hexahydrofuro[3,2-b]pyran ring system of the title compound was constructed by featuring two protocols: SHOWO (sequential hydrolysis-oxidation-Wittig olefination) and RCM (ring closing metathesis). Then, by applying a combined allylation at the anomeric position and a Pd-catalyzed double bond isomerization reaction, the methyl ester group in 1b was installed. Results: The synthesis of an advanced intermediate of MSVIII-19 involves three key procedures: A) SHOWO (sequential hydrolysis-oxidation-Wittig olefination) protocol; b) RCM (ring closing metathesis) reaction; y c) the nucleophilic substitution at the anomeric position. Additionally, with the use of a cheaper starting material (DAG) than that used in the previous synthesis (tri-O-Acetyl-D-glucal). The current synthesis is truly competitive with that reported by the Sasaki group. Conclusion: A concise formal total synthesis of the advanced intermediate of MSVIII-19 was achieved. (Current synthesis: 14 steps; previous synthesis 20 steps).

Chemical Approach to Positional Isomers of Glucose-Platinum Conjugates Reveals Specific Cancer Targeting through Glucose-Transporter-Mediated Uptake in Vitro and in Vivo

Glycoconjugation is a promising strategy for specific targeting of cancer. In this study, we investigated the effect of d-glucose substitution position on the biological activity of glucose-platinum conjugates (Glc-Pts). We synthesized and characterized all possible positional isomers (C1α, C1β, C2, C3, C4, and C6) of a Glc-Pt. The synthetic routes presented here could, in principle, be extended to prepare glucose conjugates with different active ingredients, other than platinum. The biological activities of the compounds were evaluated both in vitro and in vivo. We discovered that varying the position of substitution of d-glucose alters not only the cellular uptake and cytotoxicity profile but also the GLUT1 specificity of resulting glycoconjugates, where GLUT1 is glucose transporter 1. The C1α- and C2-substituted Glc-Pts (1α and 2) accumulate in cancer cells most efficiently compared to the others, whereas the C3-Glc-Pt (3) is taken up least efficiently. Compounds 1α and 2 are more potent compared to 3 in DU145 cells. The α- and β-anomers of the C1-Glc-Pt also differ significantly in their cellular uptake and activity profiles. No significant differences in uptake of the Glc-Pts were observed in non-cancerous RWPE2 cells. The GLUT1 specificity of the Glc-Pts was evaluated by determining the cellular uptake in the absence and in the presence of the GLUT1 inhibitor cytochalasin B, and by comparing their anticancer activity in DU145 cells and a GLUT1 knockdown cell line. The results reveal that C2-substituted Glc-Pt 2 has the highest GLUT1-specific internalization, which also reflects the best cancer-targeting ability. In a syngeneic breast cancer mouse model overexpressing GLUT1, compound 2 showed antitumor efficacy and selective uptake in tumors with no observable toxicity. This study thus reveals the synthesis of all positional isomers of d-glucose substitution for platinum warheads with detailed glycotargeting characterization in cancer.

Synthesis of Glycoconjugated Phthalonitriles for New Phthalocyanine-Based Photosensitizers

Excellent photophysical and photochemical properties completed by magnificent take-up rates in malignant tissues attracted a great deal of interest to the application of glycosylated and glycoconjugated phthalocyanines in photodynamic therapy. In this stu

Synthesis and NMR elucidation of four novel 2-(trimethylsilyl)ethyl glycosides

Four novel 2-(trimethylsilyl)ethyl glycosides have been synthesized by a short and efficient route starting from d-glucose. Their structures were elucidated by applying high-resolution mass spectra, and one-dimensional and two-dimensional NMR techniques.

Synthesis and biological activity of a novel pentacyclic heterocycle

A novel pentacyclic heterocycle has been synthesized starting from D-glucose involving two crucial conversions: the intramolecular cycloaddition of O-allyloxy furanaldoxime derived from D-glucose to furanopyran-2-isoxazoline and its diastereoselective red