79414-15-6

Upstream product

• 79414-13-4 trimethylsilylethyl bromoacetate 
• 603-35-0 triphenylphosphine 
• 2916-68-9 2-(Trimethylsilyl)ethanol 

Downstream Products

• 79414-16-7 (S)-(2E)-5-(1'-Aethoxyaethoxy)-2-hexensaeure-<(2'-trimethylsilyl)aethyl>ester 
• 631919-56-7 (3Z,2S,4S)-3-(2-phenyl-[1,3]dioxan-4-yl)-acrylic acid 2-trimethylsilanyl-ethyl ester 
• 631919-29-4 (3E,2S,4S)-3-(2-phenyl-[1,3]dioxan-4-yl)-acrylic acid 2-trimethylsilanyl-ethyl ester 
• 280762-70-1 2-(trimethylsilyl) ethyl-3-[3-(benzyloxy)-4-(chloromethyl)-5-(hydroxymethyl)-2-pyridinyl]propanoate 
• 631919-33-0 (1'S,1R,2R)-2-[3-(1-phenyl-1H-tetrazole-5-sulfonyl)-1'-triethylsilanyloxy-propyl]-cyclopentane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 631919-59-0 (1'S,1R,2R)-2-[3-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-1'-triethylsilanyloxy-propyl]-cyclopentane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 631919-58-9 (1'S,1R,2R)-2-[1'-hydroxy-3-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-propyl]-cyclopentane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 631919-31-8 2(R)-allyl-3(R)-(2(S)-phenyl-[1,3]dioxan-4(S)-yl)-pent-4-enoic acid 2-trimethylsilanyl-ethyl ester 
• 631919-32-9 1(R),2(R)-(2(S)-phenyl-[1,3]dioxan-4(S)-yl)-cyclopent-3-enecarboxylic acid 2-trimethylsilanyl-ethyl ester 

Relevant academic research and scientific papers

Oxazolidinone compound as well as preparation method, application and pharmaceutical composition thereof

The invention relates to an oxazolidinone compound used as an Lp-PLA2 covalent inhibitor and a pharmaceutical composition of the oxazolidinone compound, the structure of the oxazolidinone compound isshown as a general formula I, and R1, R2 and R3 are defined as the specification and claims. The compound shown in the general formula I or the stereoisomer or the pharmaceutically acceptable salt thereof can be used as the Lp-PLA2 covalent inhibitor to prevent and/or treat and/or improve diseases related to Lp-PLA2 enzyme activity. Meanwhile, the stereoisomer or the pharmaceutically acceptable salt of the compound shown in the general formula I can be used as an Lp-PLA2 specific molecular probe.

Structure reassignment and synthesis of jenamidines A1/A 2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues

The proposed structures of jenamidines A, B, and C (1-3) were revised to jenamidines A1/A2, B1/B2, and C (8-10). Jenamidines A1/A2 (8) were synthesized from activated proline derivative 43 by conversion to 26 in two steps and 50% overall yield. Acylation of 26 with acid chloride 38d gave 39d, which was deprotected with TFA and then mild base to give 8 in 45% yield from 26. (-)-trans-2,5- Dimethylproline ethyl ester (49) was prepared by the enantioselective Michael reaction of ethyl 2-nitropropionate (51) and methyl vinyl ketone (50) using modified dihydroquinine 60 as the catalyst. Further elaboration converted 49 to natural (+)-NP25302 (12). A Wittig reaction of proline NCA (76) with ylide 79 gave 72 as a 9/1 E/Z mixture in 27% yield, completing a one-step formal synthesis of SB-311009 analogues.

Phosphine-catalyzed synthesis of 1,3-dioxan-4-ylidenes

(Chemical Equation Presented) A phosphine-catalyzed reaction of an allenoate with aldehydes furnished (2,6-diaryl-[1,3]dioxan-4-ylidene)-acetates 4 in excellent to moderate yields with complete diastereoselectivity and high E/Z-selectivities. Upon removal of the acetal functionality in this domino reaction product 4, δ-hydroxy-β-ketoester 11 was obtained. The reported vinylphosphonium-based approach provides a new way to achieve a synthesis of δ-hydroxy-β-ketoesters that differs from the classical dianion-based approach.

Transformation of vitamin B6 to (+)-deoxypyridinoline, a useful biochemical marker for diagnosis of bone diseases

A versatile chiral synthesis of the cross-link (+)-deoxypyridinoline (Dpd, 2) was achieved starting from vitamin B6 (7). The key steps in the synthesis of (+)-2 are transformation of B6 (7) to the chloride (3d) and construction of three α-amino acid chains by utilizing (R)-(-)-Schollkopf's reagent (4), Wittig reagent (R)-(-)-5, and iodide (5)-(-)-6. (+)-Dpd (2) is a degradation product of bone collagen and has been found to be a useful marker for diagnosis of osteoporosis and other metabolic bone diseases. (C) 2000 Elsevier Science Ltd.

Enantiomerically Pure Synthetic Building Blocks with Four C-Atoms and Two or Three Functional Groups from β-Hydroxy-butanoic, Malic, and Tartaric Acid

The pool of chiral, non-racemic electrophilic building blocks, which are available from simple natural products in both enantiomeric forms is enlarged by the epoxides 3, 5, and 10, by the tosylate 12a, and by the aldehydes 18 (cf. symbols A-D, 14, and Scheme 1).Key steps of the conversions leading from hydroxyacids to the building blocks are: epoxide-opening by triethylborohydride (1 --> 2a) and tosylate reduction (12a --> 12b); the Mitsunobu inversion (2a --> 4a); the reduction of (R,R)-tartaric ester to (R)-malic ester by NBS (N-bromosuccinimide) opening of the benzaldehyde acetal 8 and tin hydride reduction (6c -->7c); the enantiomer enrichment of optically active ethyl β-hydroxy-butanoate through the crystalline dinitrobenzoate 21b.Detailed procedures are given for large scale preparations of the key intermediates.The enantiomeric purities of the building blocks are secured by correlations.