(tert-Butyldimethylsilyloxy)acetaldehyde is used in tetrahydropyran subunit construction, yielding addition products in good amounts in various total syntheses of biologically active molecules.
Used in tetrahydropyran subunit construction.
Application：
(tert-Butyldimethylsilyloxy)acetaldehyde is a versatile reagent commonly used in synthetic glycobiology. It can act both as an aldol donor and an aldol acceptor in the stereocontrolled production of erythrose. It is used as an important reagent in the total synthesis of (+)-ambruticin, (−)-laulimalide, (−)-salinosporamide A, and (+)-leucascandrolide A.
Employed in the construction of the key tetrahydropyran subunit in a recent synthesis of the marine natural product (–)-dactylodide.
| Pubchem Sid | 488194745 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/488194745 |
| Sonrisas canónicas | CC(C)(C)[Si](C)(C)OCC=O |
| IUPAC Name | 2-[tert-butyl(dimethyl)silyl]oxyacetaldehyde |
| InChIKey | MEBFFOKESLAUSJ-UHFFFAOYSA-N |
| INCHI | 1S/C8H18O2Si/c1-8(2,3)11(4,5)10-7-6-9/h6H,7H2,1-5H3 |
| Isómeros SMILES | CC(C)(C)[Si](C)(C)OCC=O |
| WGK Alemania | 3 |
| Peso molecular | 174.31 |
| Reaxy-Rn | 3536465 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3536465&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organometallic compounds |
| Clase | Organometalloid compounds |
| Subclass | Organosilicon compounds |
| Intermediate Tree Nodes | Organoheterosilanes |
| Direct Parent | Trialkylheterosilanes |
| Alternative Parents | Silyl ethers Organic metalloid salts Organic oxides Hydrocarbon derivatives Aldehydes |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Trialkylheterosilane - Silyl ether - Organic metalloid salt - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organic salt - Organooxygen compound - Carbonyl group - Aldehyde - Aliphatic acyclic compound |
| Descripción | This compound belongs to the class of organic compounds known as trialkylheterosilanes. These are organoheterosilanes, bearing a silicon atom linked to three alkyl groups and one heteroatom. |
| External Descriptors | Not available |
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Fecha | Articulo |
|---|---|---|---|
 I2412407 | Certificate of Analysis | Jun 15, 2026 | I131842 |
| I2412458 | Certificate of Analysis | Jun 15, 2026 | I131842 |
| I2412461 | Certificate of Analysis | Jun 15, 2026 | I131842 |
| I2412465 | Certificate of Analysis | Jun 15, 2026 | I131842 |
| I2412467 | Certificate of Analysis | Jun 15, 2026 | I131842 |
| C2331606 | Certificate of Analysis | Apr 09, 2023 | I131842 |
| C2331609 | Certificate of Analysis | Apr 09, 2023 | I131842 |
| C2331612 | Certificate of Analysis | Apr 09, 2023 | I131842 |
| C2331596 | Certificate of Analysis | Apr 09, 2023 | I131842 |
| C2331608 | Certificate of Analysis | Apr 09, 2023 | I131842 |
| C2331610 | Certificate of Analysis | Apr 09, 2023 | I131842 |
| Sensibilidad | moisture & heat sensitive |
|---|---|
| Índice de refracción | n20/D 1.432 (lit.) |
| Punto de inflamación (°F) | 140 °F |
| Punto de inflamación (°C) | 60 °C |
| Punto de ebullición (°C) | 65 °C/17 mmHg |
| Peso molecular | 174.310 g/mol |
| XLogP3 | |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 4 |
| Exact Mass | 174.108 Da |
| Monoisotopic Mass | 174.108 Da |
| Topological Polar Surface Area | 26.300 Ų |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Complexity | 136.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
