3, 5, 6-O-Tribenzyl-1, 2-O-isopropylidene-D-glucofuranose, CAS:53928-30-6

3,5,6-Tri-O-benzyl-1,2-O-isopropylidene-a-D-glucofuranose is a synthetic monosaccharide that has been fluorinated at the C3 position. It is an oligosaccharide with a complex carbohydrate structure. This glycosylation product can be custom synthesized and has been modified by methylation. 3,5,6-Tri-O-benzyl-1,2-O-isopropylidene Glucuronic acid can be used in the synthesis of polysaccharides or as a sugar for click chemistry. 3,5,6-tri-O-.benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose is a glycoside molecule that belongs to the class of benzyl glycosides. It is commonly used in the synthesis and characterization of various carbohydrates, glycoconjugates, and glycosamines. The molecule is structurally similar to glucose but has additional benzyl moieties on its hydroxyl groups. The compound is a colourless crystalline solid and was first synthesized in 1960 by Fischer and Zechmeister. Synthesis and Characterization: The synthesis of 3,5,6-tri-O-.benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose is mainly achieved by the benzoylation of the hydroxyl groups of ?-D-glucose followed by sequential removal of the aromatic benzyl protecting groups. The synthesis steps involve the use of various reagents such as benzoyl chloride, sodium hydroxide, and lithium aluminum hydride. Analytical Methods: Various analytical methods are used to characterize the compound, such as NMR spectroscopy, FT-IR spectroscopy, X-Ray crystallography, and mass spectrometry. The analytical techniques provide information regarding the structural integrity, purity, and composition of the compound. Biological Properties: Studies have shown that 3,5,6-tri-O-.benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose exhibits potent antitumor activities against various cancer cell lines. It also has been used as a component of glycopeptides and glycolipids having potential anti-tumour agents. Additionally, the compound has been shown to exhibit potent anti-HIV activities. Toxicity and Safety in Scientific Experiments: Safety data regarding the compound's toxicity is limited. However, the current research suggests that the compound may exhibit some level of toxicity to living cells. It is always recommended to handle the compound with appropriate caution and protective equipment. Applications in Scientific Experiments: 3,5,6-tri-O-.benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose has been widely used as a key intermediate in the synthesis of various carbohydrate compounds and glycoconjugates. Its benzyl group protection scheme enables a broad range of synthetic manipulations and has been extensively used for carbohydrate synthesis. Current State of Research: Currently, research on 3,5,6-tri-O-.benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose is mainly focused on its biological activities, synthesis and characterization of its derivatives, and its potential applications in drug discovery developments. Potential Implications in Various Fields of Research and Industry: Owing to its biological activities and synthetic properties, 3,5,6-tri-O-.benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose has great potential for applications in the fields of drug discovery, biotechnology and materials chemistry. Further research and development could enhance the utilization of the compound in these fields. Limitations and Future Directions: Currently, a major limitation in the use of the compound is its toxicity, which requires further exploration. Future research could focus on developing more facile synthesis strategies, bioconjugation strategies and designing safer derivatives that could enhance the pharmacological potential of this molecule. Additionally, the potential usefulness of 3,5,6-tri-O-.benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose in catalysis, glycoimmunology, and bacterial infections could be further explored. In conclusion, 3,5,6-tri-O-.benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose is a versatile molecule with great potential for applications in various fields of research and industry. Further research into the compound's biological activities and synthesis strategies could lead to more widespread use of the compound in these fields. CAS Number 53928-30-6 Product Name 3,5,6-tri-O-.benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose IUPAC Name (3aR,5R,6S,6aR)-5-[(1R)-1,2-bis(phenylmethoxy)ethyl]-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole Molecular Formula C30H34O6 Molecular Weight 490.59 g/mol InChI InChI=1S/C30H34O6/c1-30(2)35-28-27(33-20-24-16-10-5-11-17-24)26(34-29(28)36-30)25(32-19-23-14-8-4-9-15-23)21-31-18-22-12-6-3-7-13-22/h3-17,25-29H,18-21H2,1-2H3/t25-,26-,27+,28-,29-/m1/s1 InChI Key RNPMTPOOMRPILB-XYPQWYOHSA-N SMILES CC1(OC2C(C(OC2O1)C(COCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)C Canonical SMILES CC1(OC2C(C(OC2O1)C(COCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)C Isomeric SMILES CC1(O[C@@H]2[C@H]([C@H](O[C@@H]2O1)[C@@H](COCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)C CAS No: 53928-30-6 MDL No: MFCD08703754 Chemical Formula: C30H34O6 Molecular Weight: 490.59 COA: Product name : 3,5,6- O -Tribenzyl-1,2- O -isopropylidene-D-glucofuranose M.F. : C 30 H 34 O 6 M .W. : 490.59 CAS: 53928-30-6 Batch No : 20120101 Quantity : 16kg Items Standards Results Appearance A yellow oil Complies Solubility Readily soluble in CHC 3 and insoluble in water Positive NMR and MS Should comply Complies Identification IR and TLC Positive Residue on ignition Max. 0.5% 0.1% Heavy metal Max. 50ppm Complies TLC (15%H 2 SO 4 -C 2 H 5 OH) Should be one spot One spot