Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

449458

Sigma-Aldrich

(tert-Butyldimethylsilyloxy)acetaldehyde

90%

Synonym(s):

(tert-Butyldimethylsiloxy)acetaldehyde, 2-(tert-Butyldimethylsilyloxy)acetaldehyde, 2-[(tert-Butyl)dimethylsiloxy]acetaldehyde, 2-[(tert-Butyldimethylsilanyl)oxy]acetaldehyde, 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]acetaldehyde, Dimethyl-tert-butylsilyloxyacetaldehyde

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Linear Formula:
(CH3)3CSi(CH3)2OCH2CHO
CAS Number:
102191-92-4
Molecular Weight:
174.31
MDL number:
MFCD01321229
UNSPSC Code:
12352100
PubChem Substance ID:
24868481
NACRES:
NA.22

Assay

90%

refractive index

n20/D 1.432 (lit.)

bp

165-167 °C (lit.)

density

0.915 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)(C)[Si](C)(C)OCC=O

InChI

1S/C8H18O2Si/c1-8(2,3)11(4,5)10-7-6-9/h6H,7H2,1-5H3

InChI key

MEBFFOKESLAUSJ-UHFFFAOYSA-N

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.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

140.0 °F - closed cup

Flash Point(C)

60 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Ignace Louis et al.
Organic letters, 8(6), 1117-1120 (2006-03-10)
[reaction: see text] The enantioselective total synthesis of (-)-dactylolide is reported. The absolute stereochemistry of the tetrahydropyran was established by catalytic asymmetric Jacobsen hetero-Diels-Alder reaction. The remote C19 stereocenter was introduced by a sequence of chelation-controlled Grignard addition and Ireland-Claisen
Hisatoshi Uehara et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(48), 20672-20677 (2010-07-20)
Given the significance of carbohydrates in life, medicine, and industry, the development of simple and efficient de novo methods to synthesize carbohydrates are highly desirable. Organocatalytic asymmetric assembly reactions are powerful tools to rapidly construct molecules with stereochemical complexity from
Ritsuo Imashiro et al.
Organic letters, 12(22), 5250-5253 (2010-11-03)
Organocatalyst-controlled asymmetric anti-Michael reactions of (tert-butyldimethylsilyloxy)acetaldehyde with a range of nitroolefins, followed by an intermolecular aza-Henry reaction with imine, provided iminosugar derivatives with five contiguous stereocenters in very high enantiomeric excess in one pot. The stereochemistry of the aza-Henry reaction
Synthesis of (?)-thioascorbic acid.
Stachel H-D, et al.
Tetrahedron, 49(22), 4871-4880 (1993)
Synthesis and Biological Evaluation of the Trifluoromethyl Analog of (4S)-4, 5-Dihydroxy-2, 3-pentanedione (DPD).
Frezza M, et al.
European Journal of Organic Chemistry, 20, 4731-4736 (2006)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service