CAS 32384-65-9

2,3,4,6-Tetrakis-O-trimetilsilil-D-gluconolattone

Descrizione:

2,3,4,6-Tetrakis-O-trimetilsilil-D-gluconolattone è un derivato della D-gluconolattone, che è un estere ciclico dell'acido D-gluconico. Questo composto presenta quattro gruppi trimetilsililici (TMS) attaccati ai gruppi idrossilici della parte glucosidica, migliorando la sua stabilità e idrofobicità. La presenza di questi gruppi TMS rende il composto più adatto per l'analisi mediante cromatografia gasosa e spettrometria di massa, poiché riducono la polarità e aumentano la volatilità. La struttura della lattone contribuisce alla sua reattività, permettendogli di partecipare a varie reazioni chimiche, tra cui idrolisi ed esterificazione. Questo composto è tipicamente utilizzato nella sintesi organica e nella chimica analitica, in particolare nella derivatizzazione dei carboidrati per una migliore rilevazione e quantificazione. Le sue caratteristiche strutturali uniche lo rendono anche un intermediario prezioso nella sintesi di molecole organiche più complesse. Come molti composti organosiliconici, è importante maneggiarlo con cura, considerando la reattività potenziale e i protocolli di sicurezza.

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

Sinonimi:

• (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

Purezza: 95%

Colore e forma: Liquid

Peso molecolare: 466.8645

Ref: IN-DA0039AU

Canagliflozin Impurity 9

CAS: 32384-65-9

Formula: C₁₈H₄₂O₆Si₄

Colore e forma: Colorless Liquid

Peso molecolare: 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

Purezza: 90%

Colore e forma: clear. colourless. viscous liquid

Peso molecolare: 466.86g/mol

Ref: 54-OR53043

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

CAS: 32384-65-9

Formula: C₁₈H₄₂O₆Si₄

Purezza: >98.0%(GC)

Colore e forma: Colorless to Light yellow clear liquid

Peso molecolare: 466.87

Ref: 3B-T4205

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

CAS: 32384-65-9

Formula: C₁₈H₄₂O₆Si₄

Peso molecolare: 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

Colore e forma: Neat

Peso molecolare: 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

Purezza: Min. 95%

Colore e forma: Colorless Clear Liquid

Peso molecolare: 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

Purezza: 95%

Colore e forma: Liquid

Peso molecolare: 466.8680115

Ref: 10-F789609

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

Prodotto controllato

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

Colore e forma: Neat

Peso molecolare: 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

Colore e forma: Solid

Peso molecolare: 466.868

Ref: TM-T66182