(1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol tetraacetate
[CAS# 461432-25-7]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: (1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol tetraacetate
• Synonyms: [(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]oxan-2-yl]methyl acetate
• Molecular Formula: C₂₉H₃₃ClO₁₀
• Molecular Weight: 577.02
• CAS Registry Number: 461432-25-7
• EC Number: 930-010-9
• SMILES: CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)Cl

Properties

• Solubility: Insoluble (7.5E^-4 g/L) (25 °C), Calc.^*
• Density: 1.29±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

Safety Data

• Hazard Symbols: GHS09 Warning
• Risk Statements: H400-H410
• Safety Statements: P273-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410

Discovery and Applications

(1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol tetraacetate is a complex chemical compound notable for its diverse applications in chemical research and medicinal chemistry. The compound, with the molecular formula C26H25ClO8, features a glucose-derived anhydro sugar backbone modified with various functional groups, which confer specific properties and reactivity useful for various applications.

The discovery and synthesis of (1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol tetraacetate typically involve a multi-step synthetic route. The synthesis starts with the preparation of the anhydro sugar derivative, which involves the formation of the anhydro linkage between glucose units. Subsequent steps introduce the phenyl and ethoxy substituents through selective halogenation and alkylation reactions. The final product is obtained by acetylation of the hydroxyl groups, leading to the formation of the tetraacetate derivative. Purification is generally achieved through chromatographic techniques to ensure the desired purity and yield.

One of the primary applications of (1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol tetraacetate lies in medicinal chemistry. The compound's structure makes it a valuable intermediate for the development of pharmaceuticals. The presence of the chloro and ethoxyphenyl groups allows for the introduction of diverse functionalities, which can be tailored to enhance biological activity. The glucitol moiety, derived from glucose, can be utilized to create compounds with potential therapeutic effects, including antidiabetic, anti-inflammatory, or anticancer agents.

In addition to its role in drug development, (1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol tetraacetate is used in chemical biology and materials science. Its unique structure enables the creation of complex biomolecules and functionalized materials. The halogenated phenyl groups contribute to specific interactions with biological targets or materials, making it a useful reagent in biochemical assays or as a building block for functionalized polymers.

The compound's role in chemical synthesis also highlights its importance. Its functional groups can participate in various chemical reactions, such as nucleophilic substitutions or cross-coupling reactions. These reactions enable the formation of new chemical entities or materials with desired properties. Thus, (1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol tetraacetate serves as a versatile intermediate in the synthesis of complex molecules and materials.

In conclusion, (1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol tetraacetate is a significant chemical substance with valuable applications in medicinal chemistry, chemical biology, and materials science. Its complex structure and functional groups make it an important tool for the development of new pharmaceuticals and advanced materials.

References

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