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449458

(叔丁基二甲基硅氧基)乙醛

Name: (叔丁基二甲基硅氧基)乙醛
Brand: ALDRICH

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:

102191-92-4

分子量:

174.31

NACRES:

NA.22

PubChem Substance ID:

24868481

UNSPSC Code:

12352100

MDL number:

MFCD01321229

Assay:

90%

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属性

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

说明

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

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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One-pot enantioselective syntheses of iminosugar derivatives using organocatalytic anti-michael-anti-aza-Henry reactions.

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

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

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全球贸易项目编号

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