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Merck
CN

449458

(叔丁基二甲基硅氧基)乙醛

90%

别名:

(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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线性分子式:
(CH3)3CSi(CH3)2OCH2CHO
化学文摘社编号:
分子量:
174.31
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
90%
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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

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

存储类别

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

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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Colobert, Francoise; et al.
European Journal of Organic Chemistry, 6, 1455-1467 (2006)
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)
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)
Stereocontrolled total synthesis of (+)-leucascandrolide A.
Paterson I and Tudge M
Angewandte Chemie (International Edition in English), 115(3), 357-361 (2003)

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