2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone (Dapagliflozin Stage-3)

CAS Number: 32384-65-9

Molecular Formula: C18H42O6Si4

Purity: Dapagliflozin Stage-3 purity 93.62%

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About 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone (Dapagliflozin Stage-3)

2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone (CAS 32384-65-9) is a vital silyl-protected intermediate in the US API intermediates market, primarily utilized for the stereoselective synthesis of SGLT2 inhibitors and other C-glycoside pharmaceuticals where Pharma/API purity 99% is required to maintain strictly cont...

2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone (Dapagliflozin Stage-3) Specifications

CAS Number

32384-65-9

Molecular Formula

C18H42O6Si4

Molecular Weight

466.9 g/mol

IUPAC Name

(3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)oxan-2-one

Canonical SMILES

C[Si](C)(C)OC[C@@H]1C([C@@H](C(C(=O)O1)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C

InChI Key

VNGTZLYNGGLPIZ-WCXIOVBPSA-N

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

PubChem CID

10994280

EINECS Number

608-732-8

MDL Number

MFCD22665922

HSN No

2931900090

CAS Number

32384-65-9

Molecular Formula

C18H42O6Si4

Molecular Weight

466.9 g/mol

IUPAC Name

(3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)oxan-2-one

Canonical SMILES

C[Si](C)(C)OC[C@@H]1C([C@@H](C(C(=O)O1)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C

InChI Key

VNGTZLYNGGLPIZ-WCXIOVBPSA-N

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

PubChem CID

10994280

EINECS Number

608-732-8

MDL Number

MFCD22665922

HSN No

2931900090

Molecular Weight

466.9 g/mol

Boiling Point Moisture Content

150 - 155°C @ 0.5mmHg

Moisture Content

≤ 0.5% (Karl Fischer)

Chromatographic Purity (By GC, % Area Normalisation)

Dapagliflozin Stage-3 purity 93.62%

Purity

2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone 98% purity

Melting Point

Not specified

Boiling Point

417.2±45.0 °C at 760 mmHg

Freezing point

Flash Point

171 °C

Density

0.97 g/cm3

Precise Quality

32384-65-9

PSA

63.2 Å²

logP

5.91

Average mass

466.87 g/mol

Monoisotopic mass

466.20584519 Da

Molar mass

466.87 g/mol

Vapour pressure

0.0±1.0 mmHg at 25°C

Precautionary Statement Codes

P273, P391, and P501

Hazard Classes and Categories

Aquatic Chronic 1 (100%)

Carbohydrate Protecting Group Chemistry

Highly stable, silyl-protected precursor that allows for regiospecific reactions at the anomeric centre without interfering with the secondary hydroxyl groups

GMP Analytical Standard

Serves as a high-purity volatile derivative for GC-MS sugar profiling, ensuring precise pharmaceutical QC/QA in complex carbohydrate characterisation.

C-Glycoside Precursor

Building block for the synthesis of Dapagliflozin, ensuring a streamlined pathway from D-Gluconolactone to the final bioactive molecule

Analytical Chemistry Standards

High-purity reference material for the validation of chromatographic methods in carbohydrate research

Regiospecific C-Glycosylation

Functions as a key electrophilic building block, where silyl protecting groups prevent unwanted side reactions at secondary hydroxyl sites during nucleophilic attack

Enabling Protecting Group Chemistry

Provides a robust TMS-protected matrix that facilitates purification and handling in large-scale API manufacturing environments

Pharmaceutical Intermediate

A key building block and silylated derivative of D-gluconolactone primarily used as a precursor in the industrial synthesis of sodium-glucose cotransporter 2 (SGLT2) inhibitors, including dapagliflozin, canagliflozin, and empagliflozin, for the management of type 2 diabetes

Organic Synthesis Reagent

A protected sugar derivative employed in glycoscience and carbohydrate research for regioselective and chemoselective manipulations, such as the synthesis of trans-cyclohexane-bearing C-glucose and other complex biomolecules

Chemical Primary Standard

A high-purity reference material utilized in research laboratories and quality control for the calibration of analytical instruments and the validation of chromatographic and mass spectrometry methods.

COA

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