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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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$137.00
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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

$137.00

Available to ship onApril 22, 2025Details

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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

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.[1][2] It can act both as an aldol donor and an aldol acceptor in the stereocontrolled production of erythrose.[2] It is used as an important reagent in the total synthesis of (+)-ambruticin,[3] (−)-laulimalide,[4] (−)-salinosporamide A,[5] and (+)-leucascandrolide A.[6]
Employed in the construction of the key tetrahydropyran subunit in a recent synthesis of the marine natural product (–)-dactylodide.[7]

pictograms

FlameExclamation mark
GHS02,GHS07

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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

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Certificates of Analysis (COA)

Lot/Batch Number
0000369360
0000369360
0000176807
0000180660
0000180653

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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
Synthesis of (?)-thioascorbic acid.
Stachel H-D, et al.
Tetrahedron, 49(22), 4871-4880 (1993)
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
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)
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