132696-45-8

Basic information

• Product Name: (R)-3-(BOC-AMINO)-2-METHYLPROPIONIC ACID
• Synonyms: Boc-R-3-Aminoisobutyric acid;Propanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-, (2R)- (9CI);(r)-boc-β2-homoala-oh;3-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-2R-METHYL-PROPANOIC ACID;N3-Boc-2R-methylpropionic acid;(R)-3-(tert-ButoxycarbonylaMino)-2-Methylpropanoic acid;Boc-R-3-AMinoisobutyric acid Boc-R-3-AMinoisobutyric acid;Boc-(R)-3-AMino-2-Methylpropanoic acid
• CAS NO: 132696-45-8
• Molecular Formula: C₉H₁₇NO₄
• Molecular Weight: 203.23558
• Product Categories: N-BOC
• Mol File: 132696-45-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 88 °C(lit.)
• Boiling Point: 339.502 °C at 760 mmHg
• Flash Point: 159.125 °C
• Appearance: /
• Density: 1.102 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.461
• Storage Temp.: 2-8°C
• PKA: 4.53±0.10(Predicted)
• BRN: 7202037
• CAS DataBase Reference: (R)-3-(BOC-AMINO)-2-METHYLPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(BOC-AMINO)-2-METHYLPROPIONIC ACID(132696-45-8)
• EPA Substance Registry System: (R)-3-(BOC-AMINO)-2-METHYLPROPIONIC ACID(132696-45-8)

Safety Data

• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 132696-45-8(Hazardous Substances Data)

Usage

Description

(R)-3-(BOC-AMINO)-2-METHYLPROPIONIC ACID, also known as (R)-3-((tertButoxycarbonyl)amino)-2-methylpropanoic Acid, is an organic compound that serves as a crucial building block in the synthesis of various pharmaceutical compounds. It is characterized by its unique molecular structure, which includes a tert-butoxycarbonyl (BOC) protecting group and an amino group, making it a versatile intermediate in the development of bioactive molecules.

Uses

Used in Pharmaceutical Industry:
(R)-3-(BOC-AMINO)-2-METHYLPROPIONIC ACID is used as a key reactant for the synthesis of potent antitumor macrolides, such as cryptophycin B and arenastatin A. These macrolides have demonstrated significant anti-cancer properties and are being investigated for their potential use in cancer treatment.
Used in the Synthesis of Bioactive Molecules:
Due to its unique structure, (R)-3-(BOC-AMINO)-2-METHYLPROPIONIC ACID is also used as an intermediate in the development of other bioactive molecules with potential applications in various therapeutic areas. Its BOC protecting group and amino functionality make it a valuable component in the design and synthesis of novel pharmaceutical compounds.

InChI:InChI=1/C9H17NO4/c1-6(7(11)12)5-10-8(13)14-9(2,3)4/h6H,5H2,1-4H3,(H,10,13)(H,11,12)/t6-/m1/s1

Upstream product

• 162465-50-1 (R)-3-<(tert-butoxycarbonyl)amino>-2-methylpropan-1-ol 
• 182486-16-4 methyl 3-<<(tert-butoxy)carbonyl>amino>-2-methylpropanoate 
• 180964-67-4 ((S)-2-Methyl-4,4-diphenyl-but-3-enyl)-carbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 182486-32-4 (R)-methyl 3-{[(tert-butoxy)carbonyl]amino}-2-methylpropionate 
• 287719-29-3 [(R)-3-((R)-4-Benzhydryl-2-oxo-oxazolidin-3-yl)-2-methyl-3-oxo-propyl]-carbamic acid tert-butyl ester 
• 518038-33-0 (2R)-(3,3-dimethoxy-2-methyl-propyl)-carbamic acid tert-butyl ester 
• 865704-54-7 tert-butyl (2R)-3-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-2-methyl-3-oxopropylcarbamate 
• 2140-95-6 (R)-3-amino-2-methylpropanoic acid 
• 943154-64-1 (2S)-N-{(2R)-2-[(dibenzylamino)methyl]propanoyl}camphorsultam 
• 518038-34-1 (2-methyl-3-oxo-propyl)-carbamic acid tert-butyl ester 
• 1233234-94-0 α-(tert-butoxycarbonylaminomethyl)acrylic acid 

Downstream Products

• 2140-95-6 (R)-3-amino-2-methylpropanoic acid 
• 144-90-1 (S)-(+)-β²-homoalanine 
• 191664-17-2 (R)-2-[((R)-3-tert-Butoxycarbonylamino-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl ester 
• 186193-24-8 (S)-2-((R)-3-tert-Butoxycarbonylamino-2-methyl-propionylamino)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester 
• 245125-88-6 (2S,2'R)-benzyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}-2'-methylpropinoyl)oxy]-4-methylpentanoate 
• 281191-03-5 (2S,2'R,1''S,2''R,1''''R)1''-(3'''-{1''''-[(tert-butoxy)carbonyl]-2''''-p-methoxyphenylethylcarbamoyl}allyl)-2''-methyl-4''-phenylbut-3''-enyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}-2'-methylpropionyl)oxy]-4-methylpentanoate 
• 162465-50-1 (R)-3-<(tert-butoxycarbonyl)amino>-2-methylpropan-1-ol 

Relevant articles and documents

Highly enantioselective conjugate addition of dialkylzinc reagents to acyclic nitroalkenes: A catalytic route to β2-amino acids, aldehydes, and alcohols

Using chiral phosphoramidite ligand (S,R,R)-L1 in the conjugate addition to acyclic nitroalkenes for the first time, we obtained enantioselectivities up to 98%. The use of acyclic substrates with different dialkylzinc reagents provides a catalytic enantio

Impact on hydrogenation catalytic cycle of the R groups Cyclic feature in "r-SMS-Phos"

A series of R-SMS-Phos ligands was evaluated in the Rh(I)-catalyzed hydrogenation of a set of olefins showing a marked influence of the cyclic nature and structure of the R groups. Overall, cPen- and Cy-SMS-Phos performed efficiently, while Ph- and Bn-SMS-Phos exhibited slower kinetics and furnished lower ees also compared with C6F5CH2-SMS-Phos. The Rh(I)-(Cy-SMS-Phos) catalyst was screened under mild conditions displaying excellent enantioselectivities and high TOFs. Cases of catalysis under catalyst or substrate control were identified.

New scalable asymmetric aminomethylation reaction for the synthesis of β2-amino acids

β-Amino acids are useful tools in the design of peptidomimetics, and the development of new methods for their syntheses, particularly the synthesis of β2-amino acids, remains an important challenge. Here we report a new scalable route based on the aminomethylation of silyl ketene N,O-acetals by Mannich-type iminium electrophiles. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.