4613-78-9

Basic information

• Product Name: BETA-GENTIOBIOSE OCTAACETATE
• Synonyms: BETA-D-GENTIOBIOSE OCTAACETATE;BETA-GENTIOBIOSE OCTAACETATE;B-GENTIOBIOSE OCTAACETATE;GENTIOBIOSE OCTAACETATE, B;6-O-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL)-1,2,3,4-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSE;6-O-BETA-D-GLUCOPYRANOSYL-D-GLUCOSE OCTAACETATE;6-O-(2,3,4,6-Tetra-O-acetyl-?D-glucopyranosyl)-1,2,3,4-tetra-O-acetyl-?D-glucopyranose;.beta.-D-Glucopyranose, 6-O-(2,3,4,6-tetra-O-acetyl-.beta.-D-glucopyranosyl)-, tetraacetate
• CAS NO: 4613-78-9
• Molecular Formula: C₂₈H₃₈O₁₉
• Molecular Weight: 678.59
• Mol File: 4613-78-9.mol
• Article Data: 17

Chemical Properties

• Melting Point: 191-195°C
• Boiling Point: 661.384 °C at 760 mmHg
• Flash Point: 272.155 °C
• Appearance: /
• Density: 1.37 g/cm³
• CAS DataBase Reference: BETA-GENTIOBIOSE OCTAACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: BETA-GENTIOBIOSE OCTAACETATE(4613-78-9)
• EPA Substance Registry System: BETA-GENTIOBIOSE OCTAACETATE(4613-78-9)

Safety Data

• Hazardous Substances Data: 4613-78-9(Hazardous Substances Data)

Usage

Description

Beta-Gentiobiose octaacetate, with the chemical formula C28H36O19 and CAS number 4613-78-9, is a disaccharide derivative known for its significance in the field of organic chemistry. It is characterized by the presence of eight acetate groups, which contribute to its unique chemical properties and reactivity. beta-Gentiobiose octaacetate is derived from the natural disaccharide gentiobiose, which is composed of two glucose units. The acetylation of gentiobiose results in the formation of beta-Gentiobiose octaacetate, enhancing its stability and solubility in organic solvents.

Uses

Used in Organic Synthesis:
Beta-Gentiobiose octaacetate is utilized as a valuable disaccharide building block in the synthetic preparation of various complex molecules, including leptosin. Its unique structure and reactivity make it a versatile component in the synthesis of a wide range of organic compounds.
Used in Glycosylation Reactions:
In the field of carbohydrate chemistry, beta-Gentiobiose octaacetate is employed as a glycosyl donor for the glycosylation of alcohols. This process involves the formation of glycosidic bonds, which are crucial for the synthesis of oligosaccharides, polysaccharides, and other complex carbohydrate structures. The use of beta-Gentiobiose octaacetate in glycosylation reactions allows for the creation of diverse carbohydrate derivatives with potential applications in various industries, such as pharmaceuticals, biotechnology, and materials science.
Used in Pharmaceutical Industry:
The glycosylation of alcohols using beta-Gentiobiose octaacetate can lead to the synthesis of glycoconjugates, which are compounds consisting of a carbohydrate moiety covalently attached to a non-carbohydrate component. These glycoconjugates have significant applications in the pharmaceutical industry, as they can enhance the solubility, stability, and bioavailability of drug molecules. Additionally, glycoconjugates can improve the targeting and delivery of therapeutic agents to specific cells or tissues, thereby increasing their efficacy and reducing side effects.
Used in Biotechnology:
In the biotechnology sector, beta-Gentiobiose octaacetate can be used to synthesize glycoproteins and other carbohydrate-containing biomolecules with potential applications in drug discovery, vaccine development, and diagnostic tools. The ability to create complex carbohydrate structures using beta-Gentiobiose octaacetate allows researchers to explore the role of glycosylation in various biological processes and to develop novel bioactive molecules with improved properties.
Used in Materials Science:
The unique properties of beta-Gentiobiose octaacetate, such as its solubility in organic solvents and its reactivity in glycosylation reactions, make it a promising candidate for the development of advanced materials with specific properties. For example, the synthesis of carbohydrate-based polymers and coatings using beta-Gentiobiose octaacetate can lead to the creation of materials with enhanced biocompatibility, biodegradability, and specific interactions with biological systems.

Upstream product

• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 83-87-4 D-glucose pentaacetate 
• 54325-28-9 6-O-trityl-D-glucopyranose 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 65620-65-7 1,2,3,4-tetra-O-acetyl-D-glucopyranose 
• 2280-44-6 D-Glucose 
• 74808-10-9 2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate 
• 536-11-8 gentibiose 
• 108-24-7 acetic anhydride 
• 127-09-3 sodium acetate 
• 13100-46-4 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose 
• 37074-90-1 1,2,3,4-tetra-O-acetyl-6-O-trityl-β-D-glucopyranose 
• 7792-95-2 O⁶-β-D-glucopyranosyl-α-D-glucopyranosyl fluoride 
• 7732-18-5 water 

Downstream Products

• 220041-69-0 phenyl-[O²,O³,O⁴-triacetyl-O⁶-(tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside] 
• 137451-27-5 phenyl 2,3,4,2',3',4',6'-hepta-O-acetyl-1-thio-β-gentiobioside 
• 1436870-80-2 cyclohexyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 1470074-07-7 C₃₄H₄₀F₃NO₁₈ 
• 1470074-08-8 C₃₆H₄₆O₂₁ 
• 1470074-09-9 C₂₂H₃₂O₁₄ 
• 1552275-50-9 C₃₇H₅₄O₁₃Si 
• 1448810-97-6 m-formyl-p-hydroxy-benzyl-β-D-glucopyranosyl-(1→6)-1-thio-β-D-glucopyranoside 
• 1448810-91-0 m-formyl-p-hydroxy-benzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→6)-2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranoside 
• 1379664-83-1 (-)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3-di-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside 
• 1379664-82-0 (+)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3-di-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside 
• 1022927-33-8 (+)-menthyl 2,3,4-tri-O-acetyl-6-O-[2,3-di-O-acetyl-4,6-bis-O-(4-bromobenzoyl)-β-D-glucopyranosyl]-β-D-glucopyranoside 
• 1022927-17-8 tert-butyl 6-O-[4,6-bis-O-(4-bromobenzoyl)-β-D-glucopyranosyl]-β-D-glucopyranoside 
• 1022927-05-4 (-)-menthyl 6-O-[4,6-bis-O-(4-bromobenzoyl)-β-D-glucopyranosyl]-β-D-glucopyranoside 

Relevant articles and documents

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Deuterium labelling to extract local stereochemical information by VCD spectroscopy in the C-D stretching region: A case study of sugars

Stereochemical elucidation of molecules with multiple chiral centers is difficult. Even with VCD spectroscopy, excluding all but one diastereomeric structural candidate is challenging because the stereochemical inversion of one chiral center among many centers does not always result in noticeable differences in their VCD spectra. This work demonstrates that the introduction of a suitable VCD chromophore with absorption in the 2300-1900 cm-1 region can be used for extracting local stereochemical information and for the stereochemical assignment of the C-1 position of various sugars as a case study. Through studies on a series of epimeric pairs of monosaccharides and their derivatives, we found that the introduction of one -OCD3 group to each C-1 position produced almost mirror-image VCD patterns in the 2300-1900 cm-1 region depending on the C-1 stereochemistry irrespective of the other molecular moieties. This work also shows that comparison of the observed VCD signals and the calculated ones enables the stereochemical assignment of a chiral center in the vicinity of the chromophore. This study provides a proof of concept that the use of a VCD chromophore in the 2300-1900 cm-1 region enables the analysis of selected stereochemistry of suitable molecular systems. Further studies on this concept should lead to the development of a method useful for the structural elucidation of other types of complex molecules.

Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A: Via convergent B(C6F5)3-catalyzed glycosylation of sterically-hindered precursors

A convergent synthesis of the complex, doubly-branched pentasaccharide domain of the natural-product immunoadjuvant jujuboside A is described. The key step is a sterically-hindered glycosylation reaction between a branched trisaccharide trichloroacetimida

Thermodynamically controlled regioselective glycosylation of fully unprotected sugars through Bis(boronate) intermediates

Fully unprotected D-glucose, D-mannose, and D-fructose were regioselectively glycosylated with several phenylthioglycosides to afford glycosyl-β(1→6)-α/β-D-glucopyranose, glycosyl- β(1→1)-α-D-mannofuranoside, and glycosyl-β(1→1)- β-D-fructopyranose in goo