2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone
[CAS# 32384-65-9]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone
• Synonyms: D-2,3,4,6-Tetrakis-O-(trimethylsilyl)-gluconic acid delta-lactone; (3R,4S,5R,6R)-3,4,5-Tris[(trimethylsilyl)oxy]-6-[[(trimethylsilyl)oxy]methyl]tetrahydropyran-2-one
• Molecular Formula: C₁₈H₄₂O₆Si₄
• Molecular Weight: 466.86
• CAS Registry Number: 32384-65-9
• EC Number: 608-732-8
• SMILES: C[Si](C)(C)OC[C@@H]1[C@H]([C@@H]([C@H](C(=O)O1)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C

Properties

• Density: 0.97
• Boiling point: 417 ºC
• Flash point: 171 ºC

Safety Data

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

Hazard Classification

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

Discovory and Applicatios

2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone, commonly referred to as TMS-D-gluconolactone, is a specialized chemical compound known for its use in analytical chemistry and organic synthesis. This compound is a derivative of D-gluconolactone, a naturally occurring lactone derived from D-gluconic acid, which is widely utilized in various biochemical and industrial applications.

The discovery of 2,3,4,6-tetrakis-O-trimethylsilyl-D-gluconolactone can be attributed to the need for improved methods in the analysis and manipulation of saccharides. The modification of D-gluconolactone with trimethylsilyl (TMS) groups enhances its volatility and stability, making it more suitable for gas chromatography (GC) and mass spectrometry (MS). This derivatization process involves the reaction of D-gluconolactone with trimethylchlorosilane or other trimethylsilylating agents to introduce TMS groups at specific positions on the molecule.

The application of TMS-D-gluconolactone is particularly significant in the field of carbohydrate chemistry and analytical techniques. In gas chromatography, the TMS derivatization of saccharides such as D-gluconolactone allows for their effective separation and identification. The introduction of TMS groups reduces the polarity of the molecule, facilitating its volatilization and detection during GC analysis. This modification is crucial for the accurate and efficient analysis of complex carbohydrate mixtures.

In addition to its role in analytical chemistry, 2,3,4,6-tetrakis-O-trimethylsilyl-D-gluconolactone is used in organic synthesis as a protective group for hydroxyl functional groups. The TMS groups provide protection to the hydroxyl groups during synthetic reactions, preventing unwanted side reactions. After the desired chemical transformations are completed, the TMS groups can be removed using fluoride-based reagents to regenerate the free hydroxyl groups. This technique is valuable for the selective functionalization of carbohydrates and other organic molecules.

The use of TMS-D-gluconolactone extends to the development of new analytical methods and the optimization of existing procedures. Its role in improving the resolution and sensitivity of GC and MS techniques contributes to more precise and reliable analytical results. Additionally, its application in protecting hydroxyl groups during synthesis enhances the efficiency and selectivity of chemical transformations.

Overall, 2,3,4,6-tetrakis-O-trimethylsilyl-D-gluconolactone represents a significant advancement in carbohydrate chemistry and analytical methodologies. Its ability to facilitate the analysis of saccharides and protect functional groups in organic synthesis underscores its importance as a chemical substance with diverse applications in both research and industry.

References

2019. Synthesis of Dapagliflozin. Synfacts, 15(10).
DOI: 10.1055/s-0039-1690629

2018. Synthesis of Canagliflozin. Synfacts, 14(04).
DOI: 10.1055/s-0037-1609122

2014. Synthesis of SGLT-2 Inhibitor Empagliflozin. Synfacts, 10(12).
DOI: 10.1055/s-0034-1379221