CAS 32384-65-9

2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone

Description:

2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone is a derivative of D-gluconolactone, which is a cyclic ester of D-gluconic acid. This compound features four trimethylsilyl (TMS) groups attached to the hydroxyl groups of the glucose moiety, enhancing its stability and hydrophobicity. The presence of these TMS groups makes the compound more amenable to gas chromatography and mass spectrometry analysis, as they reduce polarity and increase volatility. The lactone structure contributes to its reactivity, allowing it to participate in various chemical reactions, including hydrolysis and esterification. This compound is typically used in organic synthesis and analytical chemistry, particularly in the derivatization of carbohydrates for improved detection and quantification. Its unique structural characteristics also make it a valuable intermediate in the synthesis of more complex organic molecules. As with many organosilicon compounds, it is important to handle it with care, considering potential reactivity and safety protocols.

Formula: C₁₈H₄₂O₆Si₄

InChI: InChI=1S/C18H42O6Si4/c1-25(2,3)20-13-14-15(22-26(4,5)6)16(23-27(7,8)9)17(18(19)21-14)24-28(10,11)12/h14-17H,13H2,1-12H3/t14-,15-,16+,17-/m1/s1

InChI key: InChIKey=VNGTZLYNGGLPIZ-WCXIOVBPSA-N

SMILES: O([Si](C)(C)C)[C@H]1[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)OC(=O)[C@@H]1O[Si](C)(C)C

Synonyms:

• (3R,4S,5R,6R)-3,4,5-Tri[(trimethylsilyl)oxy]-6-[[(trimethylsilyl)oxy]methyl]tetrahydro-2H-pyran-2-one
• (3R,4S,5R,6R)-3,4,5-Tris((Trimethylsilyl)Oxy)-6-(((Trimethylsilyl)Oxy)Methyl)Tetrahydropyran-2-One
• (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)-tetrahydropyran-2-one
• (3R,4s,5r,6r)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)tetrahydro-2h-pyran-2-one
• 2,3,4,6-Tetra-O-(trimethylsilyl)-<span class="text-smallcaps">D</span>-glucono-1,5-lactone
• 2,3,4,6-Tetrakis-O-triMethylsilyl-D-gluconolactoe
• 2,3,4,6-Tetrakis-O-trimethylsilyl-<span class="text-smallcaps">D</span>-gluconolactone
• <span class="text-smallcaps">D</span>-Gluconic acid, 2,3,4,6-tetrakis-O-(trimethylsilyl)-, δ-lactone
• D-2,3,4,6-Tetrakis-O-(Trimethylsilyl)-Gluconic Acid Delta-Lactone
• Gluconic acid, 2,3,4,6-tetrakis-O-(trimethylsilyl)-, δ-lactone, <span class="text-smallcaps">D</span>-
• Gluconic acid, 2,3,4,6-tetrakis-O-(trimethylsilyl)-, δ-lactone, D-
• D-Gluconic acid, 2,3,4,6-tetrakis-O-(trimethylsilyl)-, δ-lactone
• 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone
• (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)oxan-2-one
• Dapagliflozin Impurity 12
• (3R,5R,6R)-3,4,5-Tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
• Canagliflozin Impurity 9
• 2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-1,5-lactone

2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone

CAS: 32384-65-9

Formula: C₁₈H₄₂O₆Si₄

Purity: 95%

Color and Shape: Liquid

Molecular weight: 466.8645

Ref: IN-DA0039AU

Canagliflozin Impurity 9

CAS: 32384-65-9

Formula: C₁₈H₄₂O₆Si₄

Color and Shape: Colorless Liquid

Molecular weight: 466.87

Ref: 4Z-C-152021

(3R,4S,5R,6R)-3,4,5-tris(trimethylsilyl)oxy)-6-((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

CAS: 32384-65-9

(3R,4S,5R,6R)-3,4,5-tris(trimethylsilyl)oxy)-6-((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

Formula: C₁₈H₄₂O₆Si₄

Purity: 90%

Color and Shape: clear. colourless. viscous liquid

Molecular weight: 466.86g/mol

Ref: 54-OR53043

2,3,4,6-Tetrakis-O-trimethylsilyl-D-glucono-1,5-lactone

CAS: 32384-65-9

Formula: C₁₈H₄₂O₆Si₄

Purity: >98.0%(GC)

Color and Shape: Colorless to Light yellow clear liquid

Molecular weight: 466.87

Ref: 3B-T4205

2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone

CAS: 32384-65-9

Formula: C₁₈H₄₂O₆Si₄

Molecular weight: 466.86

Ref: ST-EA-CP-E7003

2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone

CAS: 32384-65-9

Applications 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone is an antidiabetic agent and an intermediate of Dapagliflozin (D185370). 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone acts as a reagent in the synthesis of trans-cyclohexane-bearing C-glucose as sodium glucose co-transporter 2 inhibitors.
References Shao, H., et al.: Youji Huaxue, 31, 836 (2011);

Formula: C₁₈H₄₂O₆Si₄

Color and Shape: Neat

Molecular weight: 466.86

Ref: TR-T279540

2,3,4,6-Tetra-O-trimethylsilyl-D-glucono-1,5-lactone

CAS: 32384-65-9

2,3,4,6-Tetra-O-trimethylsilyl-D-glucono-1,5-lactone is a synthetic building block which has been used to prepare C-glucosides via the nucleophilic addition of a suitably functionalised aryllithium reagent, followed by a triethylsilane reduction. Notable examples of this include the synthesis of C-glycoside intermediates which have been further elaborated to afford canagliflozin, bexagliflozin and dapagliflozin which inhibit sodium-dependant glucose co-transporter 2 (SGLT2) and are of interest as antidiabetic agents.

Formula: C₁₈H₄₂O₆Si₄

Purity: Min. 95%

Color and Shape: Colorless Clear Liquid

Molecular weight: 466.86 g/mol

Ref: 3D-MT08101

(3R,4S,5R,6R)-3,4,5-Tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

CAS: 32384-65-9

Purity: 95%

Color and Shape: Liquid

Molecular weight: 466.8680115

Ref: 10-F789609

2,3,4,6-Tetrakis-O-trimethylsilyl-L-gluconolactone

Controlled Product

CAS: 32384-65-9

Stability Moisture Sensitive
Applications 2,3,4,6-Tetrakis-O-trimethylsilyl-L-gluconolactone is an intermediate in synthesizing Ent-α-C Dapagliflozin (D185365), is an enantiomer of Dapagliflozin (D185370), a sodium-glucose transporter 2 inhibitor.
References Kasichayanula, S. et al.: Diabetes, Obesity and Metabolism 13, 47 (2011)

Formula: C₁₈H₄₂O₆Si₄

Color and Shape: Neat

Molecular weight: 466.865

Ref: TR-T279543

2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-δ-lactone

CAS: 32384-65-9

2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-delta-lactone is a useful organic compound for research related to life sciences. The catalog number is T66182 and the CAS number is 32384-65-9.

Formula: C₁₈H₄₂O₆Si₄

Color and Shape: Solid

Molecular weight: 466.868

Ref: TM-T66182