Methyl α-D-glucopyranoside

Definition

Methyl α-D-glucopyranoside is a monosaccharide derivative formed by the addition of a methyl group to the anomeric carbon of the glucose molecule in the alpha configuration. It is an important compound in the study of carbohydrate chemistry and its reactions.

5 Must Know Facts For Your Next Test

1. Methyl α-D-glucopyranoside is a stable, crystalline compound that is commonly used as a model compound in the study of carbohydrate reactivity and glycosidic bond formation.
2. The methyl group in methyl α-D-glucopyranoside is attached to the anomeric carbon of the glucose molecule, resulting in the formation of a glycosidic bond.
3. The alpha configuration of the anomeric carbon in methyl α-D-glucopyranoside means that the methyl group is in the axial position relative to the glucose ring.
4. Methyl α-D-glucopyranoside is resistant to mutarotation, as the presence of the methyl group prevents the formation of the open-chain aldehyde form of glucose.
5. Reactions of methyl α-D-glucopyranoside, such as oxidation, reduction, and substitution, can provide insights into the reactivity and behavior of monosaccharides in general.

Review Questions

• Explain the significance of the anomeric configuration in methyl α-D-glucopyranoside and how it affects the compound's properties.
  • The anomeric configuration of methyl α-D-glucopyranoside, with the methyl group in the axial position, is an important feature that contributes to the compound's stability and reactivity. The alpha configuration means that the methyl group is oriented in a specific orientation relative to the glucose ring, which can influence the molecule's interactions with other compounds and its susceptibility to various reactions. This configuration also prevents the compound from undergoing mutarotation, as the presence of the methyl group prevents the formation of the open-chain aldehyde form of glucose. Understanding the anomeric configuration is crucial for predicting and interpreting the behavior of methyl α-D-glucopyranoside in the context of carbohydrate chemistry.
• Describe how the glycosidic bond in methyl α-D-glucopyranoside affects its reactivity and potential applications.
  • The glycosidic bond formed between the anomeric carbon of glucose and the methyl group in methyl α-D-glucopyranoside is a key structural feature that influences the compound's reactivity and potential applications. This glycosidic bond is resistant to hydrolysis, making methyl α-D-glucopyranoside a useful model compound for studying the formation and stability of glycosidic linkages in more complex carbohydrate structures. Additionally, the presence of the glycosidic bond can affect the compound's ability to participate in various chemical reactions, such as substitution, oxidation, or reduction, which can provide insights into the reactivity and behavior of monosaccharides more broadly. Understanding the properties of the glycosidic bond in methyl α-D-glucopyranoside is essential for interpreting its role in carbohydrate chemistry and exploring its potential applications.
• Analyze how the unique structural features of methyl α-D-glucopyranoside, such as the anomeric configuration and the glycosidic bond, contribute to its significance in the study of 25.6 Reactions of Monosaccharides.
  • The structural features of methyl α-D-glucopyranoside, including its anomeric configuration and the presence of a glycosidic bond, make it a valuable model compound for studying the reactions of monosaccharides as described in section 25.6. The alpha configuration of the anomeric carbon and the resulting axial orientation of the methyl group provide insights into the influence of stereochemistry on the reactivity and behavior of monosaccharides. Additionally, the glycosidic bond in methyl α-D-glucopyranoside is resistant to hydrolysis, allowing researchers to investigate the formation, stability, and reactivity of these types of linkages in carbohydrate chemistry. By studying the various reactions, such as oxidation, reduction, and substitution, that can occur with methyl α-D-glucopyranoside, researchers can gain a deeper understanding of the fundamental principles governing the reactivity of monosaccharides and their derivatives, which is essential for advancing the field of carbohydrate chemistry and its applications.

Related terms

Anomeric Carbon:

The carbon atom in a monosaccharide that is bonded to two oxygen atoms, one of which is part of the ring structure and the other is a hydroxyl group or a substituent.

Glycosidic Bond:

A covalent bond formed between the anomeric carbon of a monosaccharide and the hydroxyl group of another molecule, such as another monosaccharide or an alcohol.

Mutarotation:

The spontaneous interconversion between the alpha and beta anomers of a monosaccharide in aqueous solution, resulting in the establishment of an equilibrium mixture.