112635-76-4

Usage

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 (R)-ethyl 3,4-dihydroxybutanoate 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 
• 67354-34-1 ethyl 4-benzyloxyacetoacetate 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 85518-49-6 ethyl γ-hydroxyacetoacetate 
• 225933-67-5 (S)-4-ethoxy-2-hydroxy-4-oxobutanoic acid 

Downstream Products

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

Relevant academic research and scientific papers

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.

G-A CROSSLINKING CYTOTOXIC AGENTS

The invention relates to a compound of formula (I): or salts, solvates, isomers or tautomers thereof, wherein; A is a group selected from: R1 is selected from H and halogen; either R2 is selected from -CH2-halogen, C1

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 stereoselective total synthesis of decarestrictine I

A convergent and stereoselective total synthesis of decarestrictine I, a polyketide natural product, is described. Both acid and alcohol fragments were prepared from the readily available L-malic acid via Still-Gennari olefination and Sharpless asymmetric epoxidation. The Steglich esterification and ring-closing metathesis (RCM) are employed to combine both acid and alcohol fragments. Copyright

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.

Structure elucidation and stereoselective total synthesis of pavettamine, the causal agent of gousiekte

The structure elucidation of a novel natural product pavettamine (1), the causal agent of the plant toxicosis gousiekte, is reported. The structure was defined by analysis of NMR and MS data and the relative configuration followed from the 13C NMR data of the acetonide derivative. The absolute stereochemistry was established by total synthesis from (2S)-malic acid using chiral sulfoxide methodology as (2S,4R,8R,10S)-1,11-diamino-6-aza-undecane-2,4,8,10-tetraol.

NEW COMPOUNDS FOR THE TREATMENT OF CANCER

The invention provides a method of preparing the stereoisomers of 1,11-diamino-6-aza- undecane-2,4,8,10-tetraol.

Allylic stereocontrol of the intramolecular diels-alder reaction

The stereochemical outcome of the intramolecular Diels-Alder reaction of ester-linked 1,3,8-nonatrienes can be controlled by substituants about a stereogenic center attached to Cl. The scope and limitations of this approach have been investigated, with variation in substrate structure about the allylic stereocenter and the dieno phile. The stereochemical outcomes of these reactions are explained by reference to B3LYP/6-31G(d) transition structures. New insights into the conformational preferences of allylic alcohol derivatives are reported, results which allow an explanation of the differing levels of π-diastereofacial selectivity and cis/trans (i.e. endo/exo) selectivity from the reaction.

ANALOGS OF DISCODERMOLIDE AND DICTYOSTATIN-1, INTERMEDIATES THEREFOR AND METHODS OF SYNTHESIS THEREOF

A compound of the following structure: wherein R1 is H, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, or a halogen atom; R2 is H, an alkyl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; Ra, Rb and Rc are independently an alkyl group or an aryl group; Rd is an alkyl group, an aryl group, an alkoxylalkyl group, -RiSiRaRbRc or a benzyl group, wherein Ri is an alkylene group; Re is an alkyl group, an allyl group, a benzyl group, an aryl group, an alkoxy group, or -NRgRh, wherein Rg and Rh are independently H, an alkyl group or an aryl group; R3 is (CH2)n where n is and integer in the range of 0 to 5, -CH2CH(CH3)-, -CH=CH-, -CH=C(CH3)-, or -C=-C-; R4 is (CH2)p where p is an integer in the range of 4 to 12, -(CHRkl)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5C(Rsl )=C(Rs2)C(Rs3)=C(Rs4)-, -(CHRk1 )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(RsI)CH(Rs2)C(Rs3)=C(Rs4)-, -(CHRk1)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRks)y5C(Rsl)=C(Rs2)CH(Rs3)CH(Rs4)-, -(CHRkI )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rsl)CH(Rs2)CH(Rs3)CH(R s4)-,wherein y1 and y2 are 1 and y3, y4 and y5 are independently 0 or 1, Rk1, Rk2, Rk3, Rk4 and Rk5 are independently H, CH3, or OR2a, and Rs1,Rs2, Rs3, and Rs4 are independently H or CH3, wherein R2a is H, an alkyl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; and R5 is H or OR2b, wherein R2b is H, an alkyl group, an aryl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; provided that the compound is not dictyostatin 1.

Lasonolide A: Structural revision and total synthesis

The proposed structure of lasonolide A was synthesized employing radical cyclization reactions of β-alkoxyacrylates for preparation of the tetrahydropyranyl units A and B, but the spectroscopic data did not match those of the natural product. Both enantio