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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

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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

Related Categories

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

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_germany

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

Certificates of Analysis (COA)

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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)
Total synthesis of (+)-ambruticin.
Liu P and Jacobsen EN
Journal of the American Chemical Society, 123(43), 10772-10773 (2001)
Colobert, Francoise; et al.
European Journal of Organic Chemistry, 6, 1455-1467 (2006)
Total synthesis of the microtubule-stabilizing agent (−)-Laulimalide
Paterson I, et al.
Organic Letters, 3(20), 3149-3152 (2001)
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
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