66427-91-6

Basic information

• Product Name: (2R)-2-{[6-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy}-2-phenylethanamide
• Synonyms: Benzeneacetamide, α-[(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-, (αR)-
• CAS NO: 66427-91-6
• Molecular Formula: C₂₀H₂₉NO₁₂
• Molecular Weight: 475.4438
• Mol File: 66427-91-6.mol

Chemical Properties

• Boiling Point: 800°C at 760 mmHg
• Flash Point: 437.6°C
• Density: 1.61g/cm³
• Vapor Pressure: 5.3E-27mmHg at 25°C
• Refractive Index: 1.66
• CAS DataBase Reference: (2R)-2-{[6-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy}-2-phenylethanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-{[6-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy}-2-phenylethanamide(66427-91-6)
• EPA Substance Registry System: (2R)-2-{[6-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy}-2-phenylethanamide(66427-91-6)

Safety Data

• Hazardous Substances Data: 66427-91-6(Hazardous Substances Data)

Upstream product

• 51371-34-7 amygdalin 
• 61091-11-0 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-2-((S)-cyano-phenyl-methoxy)-6-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester 
• 909100-37-4 O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranosyl)trichloroacetimidate 
• 18423-99-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl (1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranoside 
• 4358-86-5 (2R)-mandelamide 

Relevant articles and documents

Synthesis and Biological Evaluation of Cyanogenic Glycosides

An efficient procedure for the synthesis of cyanogenic glycosides with different carbohydrate units was developed. Amygdalin (3), prunasin (1), sambunigrin (2), and neoamygdalin (21) were prepared according to the elaborated method, and biological tests, including antifungal, antibacterial, and cytotoxic activities, were performed.

USE OF AMYGDALIN ANALOGUES FOR THE TREATMENT OF PSORIASIS

The compounds of formula (I), wherein n is an integer from 0 to 4; R1 is a radical selected from the group consisting of H, CH3, CH2-CH3, C(CH3)3, COOH, CONH2 and C≡CH; R2, R3, R4 and R5 ar

Synthesis and evaluation of diverse analogs of amygdalin as potential peptidomimetics of peptide T

Peptide T (ASTTTNYT) is a promising molecule to prevent the neuropsychometric symptoms of patients suffering AIDS and for the treatment of psoriasis. In order to fully prove its therapeutic benefits, efforts were put forward to design peptidomimetics of the peptide. In this direction, in a recent computational study the natural product amygdalin was identified as a prospective peptidomimetic of the peptide and later proved to exhibit a similar chemotactic profile to the peptide. However, the cyanide moiety of amygdalin provides to the molecule a toxic profile. The present study reports the synthesis of a set of amygdalin analogs lacking the cyanide group with improved chemotactic profiles.

Platinum-Catalyzed Selective Hydration of Hindered Nitriles and Nitriles with Acid- or Base-Sensitive Groups

Hindered tertiary nitriles can be hydrolyzed under neutral and mild conditions to the corresponding amides using platinum(II) catalysts with dimethylphosphine oxide or other secondary phosphine oxides (SPOs, phosphinous acids) as ligands. We have found that this procedure also works well for nitriles with acid- or base-sensitive groups, which is unprecedented in terms of yield and selectivity. The catalyst loading can be as low as 0.5 mol %. Amides are isolated as the only product in high yield, and no further hydrolysis to the corresponding acids takes place. Reactions are carried out at 80 °C but take place even at room temperature. When enantiopure secondary phosphine oxide ligands are used in the hydrolysis of racemic nitriles, no kinetic resolution is observed, presumably due to racemization of the ligand during the reaction.