124150-87-4

Basic information

• Product Name: TERT-BUTYLDIMETHYLSILYL (R)-(-)-GLYCIDY&
• Synonyms: TERT-BUTYLDIMETHYLSILYL (R)-(-)-GLYCIDY&;(R)-t-Butyldimethylsilyl Glycidil Ether;Silane, (1,1-diMethylethyl)diMethyl[(2R)-oxiranylMethoxy]-;(R)-t-ButyldiMethylsilyl Glycidyl Ether;(R)-tert-Butyldimethyl(oxiran-2-ylmethoxy)silane;(R)-tert-Butyldimethyl(oxiranylmethoxy)silane;Oxirane,2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-, (2R)-;-tert-Butyldimethyl(oxiran-2-ylmethoxy)
• CAS NO: 124150-87-4
• Molecular Formula: C₉H₂₀O₂Si
• Molecular Weight: 188.341
• Product Categories: Chiral Building Blocks;Epoxides;Organic Building Blocks
• Mol File: 124150-87-4.mol
• Article Data: 39

Chemical Properties

• Boiling Point: 195-199 °C/760 mmHg
• Flash Point: 74 °C
• Appearance: /
• Density: 0.870 g/mL at 25 °C
• Vapor Pressure: 0.298mmHg at 25°C
• Refractive Index: n20/D 1.4310
• Storage Temp.: 2-8°C
• CAS DataBase Reference: TERT-BUTYLDIMETHYLSILYL (R)-(-)-GLYCIDY&(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYLDIMETHYLSILYL (R)-(-)-GLYCIDY&(124150-87-4)
• EPA Substance Registry System: TERT-BUTYLDIMETHYLSILYL (R)-(-)-GLYCIDY&(124150-87-4)

Safety Data

• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 124150-87-4(Hazardous Substances Data)

Usage

General Description

Tert-butyldimethylsilyl (R)-(-)-glycidyl ether, also known as TBDMSE, is a chiral epoxide that is commonly used in organic synthesis. It is a derivative of glycidol and is often utilized as a protective group for alcohols and a precursor for the synthesis of various organic compounds. TBDMSE is known for its high stereoselectivity and has been widely used in the production of pharmaceuticals, agrochemicals, and other fine chemicals. Its unique structure and reactivity make it a valuable building block in the field of organic chemistry.

InChI:InChI=1/C9H20O2Si/c1-9(2,3)12(4,5)11-7-8-6-10-8/h8H,6-7H2,1-5H3/t8-/m1/s1

Upstream product

• 85807-85-8 Allyloxy-tert-butyl-dimethyl-silane 
• 556-52-5 oxiranyl-methanol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 288-32-4 1H-imidazole 
• 60456-23-7 (S)-oxiranemethanol 
• 134749-70-5 1-bromo-3-((tert-butyldimethylsilyl)oxy)propan-2-ol 
• 107-18-6 allyl alcohol 
• 123151-83-7 Toluene-4-sulfonic acid (R)-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-propyl ester 
• 57044-25-4 (R)-oxiranemethanol 
• 114413-26-2 tert-butyldimethylsilyl glycidyl ether 

Downstream Products

• 139242-75-4 (2S)-1-(tert-Butyldimethylsiloxy)-4-(phenylsulfonyl)-5-(trimethylsilyl)-2-pentanol 
• 2930-05-4 (S)-benzyl glycidyl ether 
• 115961-94-9 (2S,4R)-4-Benzenesulfonyl-1-(tert-butyl-dimethyl-silanyloxy)-4-cyclopent-1-enyl-butan-2-ol 
• 115961-94-9 (2R,4R)-4-Benzenesulfonyl-1-(tert-butyl-dimethyl-silanyloxy)-4-cyclopent-1-enyl-butan-2-ol 
• 173917-45-8 1-((tert-butyldimethylsilyl)oxy)-3-phenylpropan-2-ol 
• 173917-44-7 1-(tert-butyl-dimethylsilyloxy)-4-phenylbutan-2-ol 
• 175979-71-2 (2S,4R)-2-Benzyl-5-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 
• 185252-75-9 (S)-1-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-1-phenyl-ethylamino)-propan-2-ol 
• 203307-24-8 (S)-1-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-6-(tetrahydro-pyran-2-yloxy)-hept-4-yn-2-ol 

Relevant articles and documents

Studies toward the Synthesis of an Oxazole-Based Analog of (-)-Zampanolide

Studies are described toward the synthesis of an oxazole-based analog of (-)-zampanolide (2). Construction of (-)-dactylolide analog 22 was achieved via alcohol 5 and acid 4 through esterification and Horner-Wadsworth-Emmons (HWE)-based macrocyclization; however, attempts to attach (Z,E)-sorbamide to 22 proved unsuccessful. The C(8)-C(9) double bond of the macrocycle was prone to migration into conjugation with the oxazole ring, which may generally limit the usefulness of zampanolide analogs with aromatic moieties as tetrahydropyran replacements.

Synthesis of acylglycerol derivatives by mechanochemistry

In recent times, many biologically relevant building blocks such as amino acids, peptides, saccharides, nucleotides and nucleosides, etc. have been prepared by mechanochemical synthesis. However, mechanosynthesis of lipids by ball milling techniques has remained essentially unexplored. In this work, a multistep synthetic route to access mono- and diacylglycerol derivatives by mechanochemistry has been realized, including the synthesis of diacylglycerol-coumarin conjugates.

Synthesis method of glycerol carbonate

The invention relates to the field of glycerol carbonate, particularly a synthesis method of high-purity glycerol carbonate. According to the method, glycidol is utilized to prepare the high-purity glycerol carbonate. The method comprises the following steps: adding glycidol, triethylamine and dichloromethane into a reaction kettle, performing cooling to 0 DEG C, dropwisely adding a silyl protecting group, recovering to room temperature after the dropwise addition is finished, performing reaction over night, performing washing with water, drying and distillation to obtain silyl-protected glycidol, performing addition reaction with carbon dioxide by using a catalyst to obtain silyl-protected glycerol carbonate, performing deprotection by using an acid, and performing distillation to remove the solvent, thereby obtaining the high-purity glycerol carbonate. The method has the advantages of simple technical operation process, recyclable raw materials, high product purity and low hazard, and is suitable for industrial production.