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472654

Sigma-Aldrich

N-Boc-2-aminoacetaldehyde

95%

Sinonimo/i:

tert-Butyl N-(2-oxoethyl)carbamate

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About This Item

Formula condensata:
HCOCH2NHCO2C(CH3)3
Numero CAS:
Peso molecolare:
159.18
Numero MDL:
Codice UNSPSC:
12352100
ID PubChem:
NACRES:
NA.22

Livello qualitativo

Saggio

95%

Indice di rifrazione

n20/D 1.455 (lit.)

Gruppo funzionale

aldehyde
amine

Temperatura di conservazione

−20°C

Stringa SMILE

CC(C)(C)OC(=O)NCC=O

InChI

1S/C7H13NO3/c1-7(2,3)11-6(10)8-4-5-9/h5H,4H2,1-3H3,(H,8,10)
ACNRTYKOPZDRCO-UHFFFAOYSA-N

Informazioni sul gene

human ... CTSK(1513)

Descrizione generale

N-Boc-2-aminoacetaldehyde is an organic building block. It reacts with Horner-Wadsworth-Emmons (HWE) reagent to afford γ-aminobutyric acid (GABA)-derived α-keto amide/ester units.

Applicazioni

α-Methylenation of this amino aldehyde proceeds in a quick and efficient manner using a recently reported protocol involving formaldehyde and catalysis by either pyrrolidine proprionic acid or the dipeptide L-Pro-β-Ala.
Also used in a three-component synthesis of pyrrolidines involving 1,3-dipolar cycloaddition.
N-Boc-2-aminoacetaldehyde may be employed in the following:
  • As a starting reagent in the total synthesis of (+)-negamycin.
  • Synthesis of (E)-ethyl 4-((tert-butoxycarbonyl)amino)but-2-enoate.
  • Synthesis of 2,2′-bipyridine.
A building block in the synthesis of a protected pyrroloproline.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

235.4 °F - closed cup

Punto d’infiammabilità (°C)

113 °C - closed cup

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


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Anniina Erkkilä et al.
The Journal of organic chemistry, 71(6), 2538-2541 (2006-03-11)
A rapid and extremely convenient method for alpha-methylenation of aldehydes with aqueous formaldehyde is described. Two optimal catalytic systems are presented that allow short reaction times and afford the functionalized products in good to excellent yields (up to 99%) and
Anna Turetsky et al.
Scientific reports, 4, 4782-4782 (2014-04-25)
A number of Bruton's tyrosine kinase (BTK) inhibitors are currently in development, yet it has been difficult to visualize BTK expression and pharmacological inhibition in vivo in real time. We synthesized a fluorescent, irreversible BTK binder based on the drug
Diethyl [3-Cyano-2-Oxo-3-(Triphenylphosphoranylidene) propyl] phosphonate: A Useful Horner-Wadsworth-Emmons Reagent for alpha-Keto (Cyanomethylene)-triphenylphosphoranes from Carbonyl Compounds.
Lee K.
Bull. Korean Chem. Soc., 28(10), 1641-1641 (2007)
Claudia Karnthaler-Benbakka et al.
Angewandte Chemie (International ed. in English), 53(47), 12930-12935 (2014-08-01)
The development of receptor tyrosine-kinase inhibitors (TKIs) was a major step forward in cancer treatment. However, the therapy with TKIs is limited by strong side effects and drug resistance. The aim of this study was the design of novel epidermal
The Journal of Organic Chemistry, 70, 10869-10869 (2005)

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