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Merck
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주요 문서

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472654

Sigma-Aldrich

N-Boc-2-aminoacetaldehyde

95%

동의어(들):

tert-Butyl N-(2-oxoethyl)carbamate

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모든 사진(2)

About This Item

Linear Formula:
HCOCH2NHCO2C(CH3)3
CAS Number:
89711-08-0
Molecular Weight:
159.18
MDL number:
MFCD01321273
UNSPSC 코드:
12352100
PubChem Substance ID:
24870815
NACRES:
NA.22

Quality Level

100

분석

95%

refractive index

n20/D 1.455 (lit.)

작용기

aldehyde
amine

저장 온도

−20°C

SMILES string

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)

InChI key

ACNRTYKOPZDRCO-UHFFFAOYSA-N

유전자 정보

human ... CTSK(1513)

일반 설명

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.

애플리케이션

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

235.4 °F - closed cup

Flash Point (°C)

113 °C - closed cup

개인 보호 장비

Eyeshields, Gloves, type N95 (US)

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시험 성적서(COA)

Lot/Batch Number
MKCT3472
MKCQ7930
MKCR3358
MKCP6447
MKCN5788

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문서 라이브러리 방문

Yoshio Hayashi et al.
Chemical communications (Cambridge, England), (20)(20), 2379-2381 (2008-05-14)
Herein, we describe an efficient strategy for the total synthesis of (+)-negamycin using commercially available achiral N-Boc-2-aminoacetaldehyde as starting material with 42% overall yield for a limited number of steps.
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
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)
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
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
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