112635-76-4

Basic information

• Product Name: (R)-ethyl 3,4-dihydroxybutanoate
• Synonyms: ethyl (R)-3,4-dihydroxybutanoate
• CAS NO: 112635-76-4
• Molecular Formula: C₆H₁₂O₄
• Molecular Weight: 148.15708
• Mol File: 112635-76-4.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 278.7±25.0 °C(Predicted)
• Appearance: /
• Density: 1.171±0.06 g/cm3(Predicted)
• PKA: 13?+-.0.20(Predicted)
• CAS DataBase Reference: (R)-ethyl 3,4-dihydroxybutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-ethyl 3,4-dihydroxybutanoate(112635-76-4)
• EPA Substance Registry System: (R)-ethyl 3,4-dihydroxybutanoate(112635-76-4)

Safety Data

• Hazardous Substances Data: 112635-76-4(Hazardous Substances Data)

Usage

Description

(R)-Ethyl 3,4-dihydroxybutanoate, also known as (R)-3,4-dihydroxybutanoic acid ethyl ester, is an organic compound that serves as an essential reagent in the chemical synthesis of various pharmaceutical compounds. It is characterized by its chiral center, which gives it unique properties and makes it a valuable intermediate in the synthesis of biologically active molecules.

Uses

Used in Pharmaceutical Synthesis:
(R)-Ethyl 3,4-dihydroxybutanoate is used as a key reagent for the preparation of fostriecin, a potent antiviral and anticancer agent. It plays a crucial role in the development of this compound due to its unique structural features, which facilitate the formation of the desired pharmaceutical product.
Additionally, (R)-ethyl 3,4-dihydroxybutanoate is used in the synthesis of Coreoside D, a natural product with potential biological activities. Its involvement in the synthesis process highlights its importance in the development of novel therapeutic agents derived from natural sources.

Upstream product

• 32223-97-5 (+/-)-ethyl-3,4-epoxybutanoate 
• 691-84-9 Diethyl (S)-malate 
• 225933-67-5 (S)-4-ethoxy-2-hydroxy-4-oxobutanoic acid 
• 85518-49-6 ethyl γ-hydroxyacetoacetate 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 67354-34-1 ethyl 4-benzyloxyacetoacetate 

Downstream Products

• 58081-05-3 (R)-3-hydroxybutyrolactone 
• 167167-24-0 (S)-3,4-Bis-benzyloxy-butyric acid ethyl ester 
• 182687-09-8 (S)-4-(4-Fluoro-phenoxy)-3-hydroxy-butyric acid ethyl ester 
• 188635-30-5 ethyl 4-[(tert-butyldimethylsilyl)oxy]-(3R)-2-hydroxybutanoate 
• 112348-03-5 (R)-3-Hydroxy-4-triisopropylsilanyloxy-butyric acid ethyl ester 
• 112348-04-6 ethyl (S)-4-benzyloxy-3-hydroxybutanoate 
• 106058-91-7 (+)-(R)-ethyl 4-benzyloxy-3-hydroxybutanoate 
• 299159-65-2 ethyl (3S)-4-tert-butyldimethylsiloxy-3-(diphenylvinylsiloxy)butanoate 
• 299159-70-9 ethyl (2R,3S)-4-tert-butyldimethylsiloxy-3-diphenylvinylsiloxy-2-methylbutanoate 
• 70005-88-8 (R)-1,2,4-butanetriol 
• 155872-02-9 C₁₁H₁₆O₅S 
• 133149-03-8 (S)-3-Hydroxy-4-(toluene-4-sulfonyloxy)-butyric acid ethyl ester 
• 6290-03-5 (R)-butane-1,3-diol 
• 5469-16-9 (3S)-hydroxy-γ-butyrolactone 

Relevant articles and documents

A Concise Stereoselective Total Synthesis of Methoxyl Citreochlorols and Their Structural Revisions

A concise, stereoselective and protecting group free approaches for the total synthesis of (?)-(2S,4R)- and (+)-(2R,4S)-3′-methoxyl citreochlorols and their stereoisomers are demonstrated. All four stereoisomers were synthesized to establish the absolute stereochemistry of the reported structures and the structures were revised accordingly. The approach involves chelation controlled regioselective reduction of a diester, silyl iodide promoted ring-opening iodo esterification of lactones, highly chemo- and regioselective ring-opening of an epoxy ester, dichloromethylation of a carboxyl group, and syn- and anti-selective reduction of the resulted β-hydroxy ketone as key steps.

Design, Synthesis, and Evaluation of Tetrahydropyrrolo[1,2-c]pyrimidines as Capsid Assembly Inhibitors for HBV Treatment

The discovery of novel tetrahydropyrrolo[1,2-c]pyrimidines derivatives from Bay41-4109 as hepatitis B virus (HBV) inhibitors is herein reported. The structure-activity relationship optimization led to one highly efficacious compound 28a (IC50 = 10 nM) with good PK profiles and the favorite L/P ratio. The hydrodynamic injection model in mice clearly demonstrated the efficacy of 28a against HBV replication.

A new strategy for the synthesis of crucigasterin A, and cytotoxic activity of this compound and its related analogues

Stereoselective total synthesis of bioactive marine natural product crucigasterin A has been accomplished from commercially available and inexpensive l-(-)-malic acid as a starting material. Julia olefination and chelation controlled Grignard additions are the key steps involved in the present synthesis. Cytotoxic properties of crucigasterin A and its related analogues crucigasterins B and D have been evaluated. Crucigasterin A showed promising activities against both the human cervical cancer cell line and human breast adenocarcinoma cell line.