32469-28-6

Basic information

• Product Name: (3R,4S,5R,6R)-3,4,5-tris(triMethylsilyloxy)-6-((triMethylsilyloxy)Methyl)tetrahydro-2H-pyran-2-one
• Synonyms: D-Mannonic acid, 2,3,4,6-tetrakis-O-(trimethylsilyl)-, δ-lactone
• CAS NO: 32469-28-6
• Molecular Formula: C₁₈H₄₂O₆Si₄
• Molecular Weight: 466.86448
• EINECS: 1806241-263-5
• Mol File: 32469-28-6.mol
• Article Data: 92

Chemical Properties

• Boiling Point: 417.2±45.0 °C(Predicted)
• Appearance: /
• Density: 0.97±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (3R,4S,5R,6R)-3,4,5-tris(triMethylsilyloxy)-6-((triMethylsilyloxy)Methyl)tetrahydro-2H-pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S,5R,6R)-3,4,5-tris(triMethylsilyloxy)-6-((triMethylsilyloxy)Methyl)tetrahydro-2H-pyran-2-one(32469-28-6)
• EPA Substance Registry System: (3R,4S,5R,6R)-3,4,5-tris(triMethylsilyloxy)-6-((triMethylsilyloxy)Methyl)tetrahydro-2H-pyran-2-one(32469-28-6)

Safety Data

• Hazardous Substances Data: 32469-28-6(Hazardous Substances Data)

Usage

General Description

The chemical (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)tetrahydro-2H-pyran-2-one is a compound with a complex structure containing multiple trimethylsilyloxy groups. It is a tetrahydro-2H-pyran-2-one derivative, which is a cyclic organic compound. The presence of trimethylsilyloxy groups indicates that the compound has been modified with trimethylsilyl (TMS) groups, which are often used as protective groups in organic synthesis to shield reactive functional groups from unwanted reactions. The compound's stereochemistry is defined by the (3R,4S,5R,6R) configuration, indicating the positioning of various functional groups on the tetrahydro-2H-pyran-2-one ring. This chemical may have potential applications in organic synthesis, medicinal chemistry, or materials science due to its unique structure and functional groups.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 90-80-2 D-Glucono-1,5-lactone 
• 1335-57-5 3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 15892-28-1 (3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-one 
• 18156-74-6 1-(Trimethylsilyl)imidazole 

Downstream Products

• 1050200-97-9 1-bromo-3-(4-ethylbenzyl)-5-(1-methoxy-D-glucopyranos-1-yl)-2-methyl-benzene 
• 1359948-56-3 C₄₀H₇₃BrO₉Si₅ 
• 1254333-04-4 (3R,4S,5S,6R)-6-hydroxymethyl-2-methoxy-2-[4-(4-methoxybenzyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]tetrahydropyran-3,4,5-triol 
• 1254333-65-7 (3R,4S,5S,6R)-2-[1-(4-ethylbenzyl)-1,2,3,4-tetrahydroquinolin-7-yl]-6-hydroxymethyl-2-methoxytetrahydropyran-3,4,5-triol 
• 1254333-77-1 (3R,4S,5S,6R)-6-hydroxymethyl-2-methoxy-2-[1-(4-methoxybenzyl)-1,2,3,4-tetrahydroquinolin-7-yl]tetrahydropyran-3,4,5-triol 
• 915095-95-3 1-chloro-4-(1-methoxy-D-glucopyranos-1-yl)-2-(4-(R)-tetrahydrofuran-3-yloxy-benzyl)-benzene 
• 864070-37-1 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 912917-83-0 (3R,4S,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 

Relevant articles and documents

Preparation method and application of 2, 3, 4, 6-tetra-O-trimethylsilyl-D-glucolactone

The invention relates to the technical field of medicine, in particular to a preparation method and application of 2, 3, 4, 6-tetra-O-trimethylsilyl-D-gluconolactone. According to the preparation method, D-gluconolactone and hexamethyldisilazane react in an ionic liquid, cations in the ionic liquid are alkyl imidazolium ions, and anions in the ionic liquid are hexafluorophosphate radicals, tetrafluoroborate radicals, tetrachloroaluminate radicals or chloride ions. The ionic liquid is stable during high-temperature distillation, the solvent after reaction can be recycled, the preparation methodhas few reaction steps, atom economy is high, and operation conditions are easy to control. The preparation method can be used for preparing canagliflozin.

Synthesis method and application of 1-methyl glucose

The invention discloses a synthesis method and application of 1-methyl glucose. The synthesis method comprises the following steps: dissolving gluconic acid delta-lactone in THF, adding N-methylmorpholine and TMSCl, reacting to obtain TMS-protected gluconic acid delta-lactone, dissolving the TMS-protected gluconic acid delta lactone in anhydrous THF, treating with methyl lithium or methyl magnesium bromide, reacting to obtain TMS-protected 1-methyl glucose, dissolving the TMS-protected 1-methyl glucose in acetonitrile-water, and removing TMS protection by adding H strong cation exchangeresin to obtain 1-methyl glucose. The effect of applying 1-methyl glucose to cigarette perfuming is mainly to improve the aroma quality and aroma quantity, reduce irritation and purify the aftertaste.

Telescoped lithiation, C-arylation and methoxylation in flow-batch hybrid toward the synthesis of canagliflozin

We report a highly efficient three-step flow-batch hybrid procedure for the synthesis of a key canagliflozin intermediate. The telescoped process provides exquisite control over an exothermic and mixing sensitive lithiation and subsequent C-arylation within a microstructured flow reactor. Methoxylation reagents are then added in flow, before reaching completion in a batch vessel. The flow process afforded the target intermediate in 76% yield, with a throughput of 26.8 g/h.