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
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
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
Synthesis of (?)-thioascorbic acid.
Stachel H-D, et al.
Tetrahedron, 49(22), 4871-4880 (1993)
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
Total synthesis of (+)-ambruticin.
Liu P and Jacobsen EN
Journal of the American Chemical Society, 123(43), 10772-10773 (2001)
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