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Merck
CN

449458

(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

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About This Item

Linear Formula:
(CH3)3CSi(CH3)2OCH2CHO
CAS Number:
102191-92-4
Molecular Weight:
174.31
NACRES:
NA.22
PubChem Substance ID:
24868481
UNSPSC Code:
12352100
MDL number:
MFCD01321229
Assay:
90%

Key Documents

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InChI

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

SMILES string

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

InChI key

MEBFFOKESLAUSJ-UHFFFAOYSA-N

assay

90%

refractive index

n20/D 1.432 (lit.)

bp

165-167 °C (lit.)

density

0.915 g/mL at 25 °C (lit.)

functional group

aldehyde

storage temp.

2-8°C

Quality Level

200

Related Categories

Application

Employed in the construction of the key tetrahydropyran subunit in a recent synthesis of the marine natural product (–)-dactylodide.
(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.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

140.0 °F - closed cup

flash_point_c

60 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000369360
0000369360
0000200808
0000188042
0000180653

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Enantioselective organocatalytic direct aldol reactions of α-oxyaldehydes: step one in a two-step synthesis of carbohydrates.
Northrup AB, et al.
Angewandte Chemie (International Edition in English), 43(16), 2152-2154 (2004)
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
Total synthesis of (+)-ambruticin.
Liu P and Jacobsen EN
Journal of the American Chemical Society, 123(43), 10772-10773 (2001)
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)
Entry to Heterocycles Based on Indium-Catalyzed Conia-Ene Reactions: Asymmetric Synthesis of (−)-Salinosporamide A.
Takahashi K, et al.
Angewandte Chemie (International Edition in English), 47(33), 6244-6246 (2008)
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