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449458

(tert-Butyldimethylsilyloxy)acetaldehyde

Name: (<I>tert</I>-Butyldimethylsilyloxy)acetaldehyde
Brand: ALDRICH

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%

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Properties

Quality Level

200

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

Description

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

GHS02,GHS07

signalword

Warning

hcodes

H226,H315,H319,H335

pcodes

P210 - P233 - P240 - P241 - P303 + P361 + P353 - P305 + P351 + P338

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

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Organocatalytic asymmetric assembly reactions for the syntheses of carbohydrate derivatives by intermolecular Michael-Henry reactions.

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

Enantioselective total synthesis of (-)-dactylolide.

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)

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Global Trade Item Number

SKU	GTIN
449458-1G	04061836685423
449458-5G	04061832323299