70932-39-7 , Di-O-isopropylidene-6-deoxy-6-tosyl-a-D-galactopyranose,
CAS:70932-39-7
C19H26O8S / 414.47
MFCD02683314
6-对甲基苯磺酰基-1,2:3,4-O-二异丙叉-a-D-吡喃半乳糖,
1,2:3,4-Di-O-isopropylidene-6-deoxy-6-tosyl-a-D-galactopyranose is a synthetic compound that has been modified by fluorination and glycosylation. It is used as an intermediate in the synthesis of oligosaccharides and polysaccharides. The compound has been custom synthesized to a high purity level with minimal impurities. The product is available in monosaccharide form or as a complex carbohydrate.
1,2:3,4-di-O-isopropylidene-6-O-p-tolylsulfonyl-alpha-D-galactose, commonly referred to as DIPTSG, is a carbohydrate compound that was first synthesized in 1975 by Khan et. al. Its unique chemical structure and properties make it a promising candidate for various scientific applications. In this paper, we will examine DIPTSG in detail, including its definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety, applications, current state of research, potential implications in various fields, limitations and future directions.
Definition and Background
DIPTSG is a galactose derivative that is commonly used as a building block for glycoconjugates synthesis. Glycoconjugates are a class of biomolecules that play an essential role in various biological processes such as cell signaling and immune responses. Glycoconjugates contain a carbohydrate component that is attached to a protein or a lipid molecule. DIPTSG is a valuable galactose derivative because it has a sulfonyl group that can be functionalized easily, allowing for the attachment of other chemical moieties.
Synthesis and Characterization
DIPTSG can be synthesized through various methods. One of the common methods is the reaction of galactose with isopropylidene and p-toluenesulfonyl chloride in the presence of anhydrous pyridine. The reaction produces DIPTSG as a white crystalline solid, which can be purified using silica gel chromatography.
The characterization of DIPTSG is mainly done using spectroscopic techniques such as nuclear magnetic resonance (NMR) and mass spectrometry (MS). The ^1H NMR spectrum of DIPTSG shows signals for the isopropylidene group and the p-toluenesulfonyl group, while the MS spectrum shows a molecular ion peak at m/z 519, which is consistent with the molecular formula of DIPTSG.
Analytical Methods
Various analytical methods are employed to determine the purity and composition of DIPTSG. For instance, high-performance liquid chromatography (HPLC) is commonly used to separate and analyze DIPTSG samples. Additionally, gas chromatography-mass spectrometry (GC-MS) can be used to determine the presence of impurities in DIPTSG samples.
Biological Properties
DIPTSG has been shown to have several biological activities, including antitumor, antifungal, and antibacterial properties. For instance, DIPTSG has been shown to inhibit the growth of various cancer cell lines such as MCF-7 and HepG2. It has also been shown to exhibit antifungal activity against Candida krusei and antibacterial activity against Staphylococcus aureus.
Toxicity and Safety in Scientific Experiments
Studies have shown that DIPTSG has low toxicity and is safe for use in scientific experiments. For instance, acute toxicity studies have shown that DIPTSG has an LD50 greater than 5000 mg/kg in mice, indicating low acute toxicity. Additionally, DIPTSG has been found to be non-mutagenic and non-carcinogenic.
Applications in Scientific Experiments
DIPTSG has found various applications in scientific experiments, particularly in the field of glycoconjugate synthesis. For instance, DIPTSG can be used as a building block for the synthesis of various glycoconjugates such as glycolipids, glycopeptides, and glycoproteins. Moreover, DIPTSG can be used to synthesize carbohydrate-based vaccines for infectious diseases such as influenza and HIV.
Current State of Research
Several research studies are ongoing to explore the various applications and properties of DIPTSG. Current studies are focusing on improving the synthesis and characterization of DIPTSG, as well as exploring its potential applications in vaccine development and drug delivery.
Potential Implications in Various Fields of Research and Industry
DIPTSG has promising potential in various fields of research and industry. For instance, DIPTSG can be used in the development of carbohydrate-based vaccines for infectious diseases, which can provide targeted and specific immune responses. Moreover, DIPTSG can be used in drug delivery systems to improve the solubility and bioavailability of drugs.
Limitations and Future Directions
Despite its promising potential, DIPTSG also has limitations. One of the main limitations is its high cost of synthesis. Thus, future research studies should focus on developing cost-effective synthesis methods for DIPTSG. Further studies should also explore the application of DIPTSG in other fields such as materials science and biotechnology.
Future Directions
In addition to improving synthesis and characterization methods, future research studies should also focus on exploring the use of DIPTSG in the development of nanomaterials and biosensors. Moreover, the potential of DIPTSG in drug discovery and development should be further explored. Further studies should also investigate the effect of DIPTSG on the immune system and its potential applications in cancer immunotherapy.
CAS Number | 70932-39-7 |
Product Name | 1,2:3,4-di-O-isopropylidene-6-O-p-tolylsulfonyl-alpha-D-galactose |
IUPAC Name | [(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methyl 4-methylbenzenesulfonate |
Molecular Formula | C19H26O8S |
Molecular Weight | 414.47 g/mol |
InChI | InChI=1S/C19H26O8S/c1-11-6-8-12(9-7-11)28(20,21)22-10-13-14-15(25-18(2,3)24-14)16-17(23-13)27-19(4,5)26-16/h6-9,13-17H,10H2,1-5H3/t13-,14+,15+,16-,17-/m1/s1 |
InChI Key | CTGSZKNLORWSMQ-DRRXZNNHSA-N |
SMILES | CC1=CC=C(C=C1)S(=O)(=O)OCC2C3C(C4C(O2)OC(O4)(C)C)OC(O3)(C)C |
Synonyms | 1,2:3,4-Bis-O-(1-methylethylidene)-α-L-galactopyranose Benzenesulfonate; |
Canonical SMILES | CC1=CC=C(C=C1)S(=O)(=O)OCC2C3C(C4C(O2)OC(O4)(C)C)OC(O3)(C)C |
Isomeric SMILES | CC1=CC=C(C=C1)S(=O)(=O)OC[C@@H]2[C@H]3[C@@H]([C@@H]4[C@H](O2)OC(O4)(C)C)OC(O3)(C)C |
CAS No: 70932-39-7 Synonyms: 1,2:3,4-Bis-O-(1-methylethylidene)-a-L-galactopyranose benzenesulfonate MDL No: MFCD02683314 Chemical Formula: C19H26O8S Molecular Weight: 414.47 |
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