39613-92-8

Basic information

• Product Name: D-Alanine Isopropyl Ester HCl
• Synonyms: D-Alanine Isopropyl Ester HCl;D-Alanine isopropyl ester (hydrochloride);H-D-Ala-OiPro.HCl;H-D-Ala-OiPr·HCl;(R)-isopropyl 2-aminopropanoate hydrochloride;propan-2-yl (2R)-2-aminopropanoate hydrochloride;D-ALa-Oipr. HCL;Tenofovir Impurity 7 HCl
• CAS NO: 39613-92-8
• Molecular Formula: C₆H₁₃NO₂*ClH
• Molecular Weight: 167.63386
• Mol File: 39613-92-8.mol
• Article Data: 29

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: D-Alanine Isopropyl Ester HCl(CAS DataBase Reference)
• NIST Chemistry Reference: D-Alanine Isopropyl Ester HCl(39613-92-8)
• EPA Substance Registry System: D-Alanine Isopropyl Ester HCl(39613-92-8)

Safety Data

• Hazardous Substances Data: 39613-92-8(Hazardous Substances Data)

Usage

Uses

D-Alanine Isopropyl Ester Hydrochloride is a chiral reagent used in the synthesis of nucleotide prodrugs such as (PSI-7977) for the treatment of hepatitis C. Also used in the preparation of synthetic sweeteners.

Upstream product

• 67-63-0 isopropyl alcohol 
• 2224-52-4 L-alanine N-carboxyanhydride 
• 56-41-7 L-alanin 
• 338-69-2 D-Alanine 

Downstream Products

• 86323-54-8 (S)-isopropyl 2-(4-nitrobenzamido)propanoate 
• 1444430-48-1 (S)-2-{[(2R,3S,4S,5R)-2-azido-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-fluoro-4-hydroxy-tetrahydro-furan-2-ylmethoxy]-phenoxy-phosphorylamino}-propionic acid isoropyl ester 
• 1444430-60-7 (S)-2-{[(2R,3S,4S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-azido-3-fluoro-4-hydroxy-tetrahydro-furan-2-ylmethoxy]-phenoxy-phosphorylamino}-propionic acid isopropyl ester 
• 2053424-88-5 (((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)-D-alanine isopropyl ester 
• 1337529-56-2 (S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester 

Relevant articles and documents

Evaluation of chiral amino acid discrimination by a permethylated cyclic tetrasaccharide, cyclo-{→6)-α-D-Glcp-(1→3)-α-D-Glcp- (1→6)-α-D-Glcp-(1→3)-α-D-Glcp-(1→}, using FAB mass spectrometry

The novel cyclic oligosaccharide, permethylated tetrasaecharide (CTS), determinates the enantiomers of chiral amino acid isopropyl ester hydrochlorides. Copyright

Re-Engineering Organocatalysts for Asymmetric Friedel-Crafts Alkylation of Indoles through Computational Studies

The discovery of efficient organocatalysts is generally carried out by thorough experimental screening of different candidates. We recently reported an efficient organocatalyst for iminium-ion-based asymmetric Diels-Alder reactions following a rational design approach. This result encouraged us to test this optimal catalyst in the mechanistically related Friedel-Crafts alkylation of indoles, but to our surprise, almost null enantioselectivity was observed. The results did not significantly improve with structurally related catalysts, and a totally unexpected facial selectivity inversion was also noticed. Using DFT calculations by modeling the competing transition structures with ONIOM, we could unravel the origins of those findings, further employed to predict the most efficient catalyst for this new transformation. The computational results were validated experimentally (up to 92:8 er), providing another successful example of a general strategy to accelerate catalyst development which still remains underexplored.

Stereoselective Synthesis of Sofosbuvir through Nucleoside Phosphorylation Controlled by Kinetic Resolution

The preparation of Sofosbuvir, the potent key component of recent Hepatitis C (HCV) infection therapies, is reported. The process is based on the dynamic kinetic resolution of the stereochemically unstable isopropyl-2-{[chloro(phenoxy)phosphoryl]-amino}propanoate (8). A high stereoselectivity was obtained when the right protective group for 3′-OH was chosen. Ester and carbonate-based protective groups gave lower stereoselectivities, but benzyl protection allowed the phosphorylation to occur with a 92:8 ratio in favour of the product with the right configuration at the P-stereogenic centre. Starting from the γ-lactone of 2-deoxy-2-fluoro-2-methylpentonic acid, the synthesis was accomplished in eight steps in 40 % overall yield using commercially available reagents, and without any enzymatic or chemical resolution technique.