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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关于此项目
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%
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.
signalword
Warning
hcodes
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
新产品
此项目有
Colobert, Francoise; et al.
European Journal of Organic Chemistry, 6, 1455-1467 (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)
Stereocontrolled total synthesis of (+)-leucascandrolide A.
Paterson I and Tudge M
Angewandte Chemie (International Edition in English), 115(3), 357-361 (2003)
Total synthesis of the microtubule-stabilizing agent (−)-Laulimalide
Paterson I, et al.
Organic Letters, 3(20), 3149-3152 (2001)
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
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