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  • 14227-66-8 , a-溴代纤维二糖 , Acetobromo-D-cellobiose, CAS:14227-66-8
14227-66-8 , a-溴代纤维二糖 , Acetobromo-D-cellobiose, CAS:14227-66-8

14227-66-8 , a-溴代纤维二糖 , Acetobromo-D-cellobiose, CAS:14227-66-8

14227-66-8 , Acetobromo-D-cellobiose,
a-溴代纤维二糖 ,
CAS: 14227-66-8
C26H35BrO17 / 699.45
MFCD00069839

a-溴代纤维二糖,  2,3,6,2',3',4',6'-Hepta-O-acetyl-a-D-cellobiosyl bromide

2,3,6,2',3',4',6'-Hepta-O-acetyl-a-D-cellobiosyl bromide is a naturally occurring trisubstituted steroidal glycoside. It is insoluble in water and activated by chloride ions. 2,3,6,2',3',4',6'-Hepta-O-acetyl-a-D-cellobiosyl bromide has been shown to have antiviral properties in mammalian tissue cultures. This compound also has potential use as an ingredient in skin care products due to its ability to inhibit the production of fatty acids that are essential for the replication of viruses. 2,3,6,2',3',4',6'-Hepta-O-acetyl-a-D-cellobiosyl bromide can be found in microalgae and food composition as a nutrient.

Alpha-D-Cellobiosyl bromide heptaacetate (CBHA) is a synthetic compound formed by the acetylation of a natural disaccharide containing glucose. The compound is mainly used in organic synthesis as a source of the cellobiose and acetyl group. The alpha-D-Cellobiosyl bromide heptaacetate molecule is composed of two glucose monomers joined by a glycosidic bond in an alpha-1,4 configuration. The cellobiose molecule contains a hydroxyl group on each glucose residue, which can be acetated under acetylation conditions. CBHA is a white crystalline powder, soluble in organic solvents like methanol, ethanol, and chloroform.

Synthesis and Characterization

CBHA is synthesized by the acetylation of cellobiose with acetic anhydride and bromine in an organic solvent. The process is performed under anhydrous and acidic conditions to avoid hydrolysis. 

The formation of CBHA is confirmed by various characterization techniques, including infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS). The IR spectrum of CBHA shows typical absorption bands for C=O stretching, C-O stretching, and C-H bending. The NMR spectrum of CBHA confirms the structure of the molecule, and the MS spectrum provides the molecular weight of the compound.

Analytical Methods

CBHA can be analyzed using various analytical techniques, including chromatography and spectrometry. High-performance liquid chromatography (HPLC) and gas chromatography (GC) are commonly used to separate and quantify CBHA. The compound can also be analyzed by mass spectrometry (MS), nuclear magnetic resonance (NMR) spectroscopy, and infrared (IR) spectroscopy.

Biological Properties

CBHA has not been extensively studied for its biological properties. However, some studies have reported that the compound has biological activities, including antioxidant and anticancer properties.

Toxicity and Safety in Scientific Experiments

CBHA has a low toxicity profile and is considered safe for use in scientific experiments. However, it should be handled with care since the compound is sensitive to light, heat, and humidity.

Applications in Scientific Experiments

CBHA is commonly used as a synthetic intermediate in organic synthesis, particularly for the synthesis of carbohydrate-containing molecules, glycoside mimetics, and oligoaccharides. CBHA is also used as a cell-permeable substrate for enzymes involved in polysaccharide degradation. It is also used as a chiral auxiliary in asymmetric synthesis.

Current State of Research

Currently, research on CBHA is relatively limited. Most studies have focused on the synthesis and characterization of the compound. However, there is ongoing research on the applications of CBHA in organic synthesis, including the development of new glycosylation methods and the synthesis of glycosides.

Potential Implications in Various Fields of Research and Industry

CBHA has potential applications in various fields of research and industry, including organic synthesis, drug discovery, and immunology. The compound can be used to synthesize glycoside-containing molecules, which are important in drug discovery and immunological research.

Limitations and Future Directions

CBHA has some limitations in its use as a substrate for enzymes involved in polysaccharide degradation. The compound is not a natural substrate, and thus, its compatibility with different enzymes needs to be evaluated. Future directions of research on CBHA include the development of new synthetic methods, the synthesis of novel glycosides, and the evaluation of its potential biological activities.

List of Future Directions:

1. The development of new synthetic methods for CBHA.

2. The synthesis of novel glycosides using CBHA.

3. The evaluation of CBHA's compatibility with different enzymes.

4. The evaluation of CBHA's potential biological activities in-vitro and in-vivo.

5. The development of new glycosylation methods using CBHA.

6. The evaluation of CBHA's potential use as a cell-permeable substrate in biological assays.

7. The development of new CBHA derivatives for specific applications.

8. The integration of CBHA in carbohydrate-based vaccine design.

9. The use of CBHA in the development of bioactive materials.

10. The evaluation of CBHA's potential as an antifungal agent.

CAS Number14227-66-8
Product Namealpha-D-Cellobiosyl bromide heptaacetate
IUPAC Name[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-bromooxan-3-yl]oxyoxan-2-yl]methyl acetate
Molecular FormulaC26H35BrO17
Molecular Weight699.45 g/mol
InChIInChI=1S/C26H35BrO17/c1-10(28)35-8-17-20(21(38-13(4)31)23(25(27)42-17)40-15(6)33)44-26-24(41-16(7)34)22(39-14(5)32)19(37-12(3)30)18(43-26)9-36-11(2)29/h17-26H,8-9H2,1-7H3/t17-,18-,19-,20-,21+,22+,23-,24-,25+,26+/m1/s1
InChI KeyNLFHLQWXGDPOME-VRECAULFSA-N
SMILESCC(=O)OCC1C(C(C(C(O1)OC2C(OC(C(C2OC(=O)C)OC(=O)C)Br)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
Synonymsalpha-D-cellobiosyl bromide heptaacetate, Cel Br heptaacetate, cellobiosyl bromide heptaacetate
Canonical SMILESCC(=O)OCC1C(C(C(C(O1)OC2C(OC(C(C2OC(=O)C)OC(=O)C)Br)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
Isomeric SMILESCC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@@H]([C@@H]([C@H]2OC(=O)C)OC(=O)C)Br)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
CAS No: 14227-66-8 Synonyms: Acetobromo-D-cellobiose MDL No: MFCD00069839 Chemical Formula: C26H35BrO17 Molecular Weight: 699.45
References: 1. Hou Z, Liang L, Chin. Lett. 2003, Vol14, No3, p229-232

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