270902-66-4

Usage

Uses

Used in Organic Synthesis:
(4S,4aR,7R,7aR)-7-Methoxy-2,2-diMethyl-6-oxo-tetrahydro-4H-furo[3,2-d][1,3]dioxine-4-carbaldehyde is utilized as a key intermediate in organic synthesis for the development of novel compounds with potential applications in various industries.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (4S,4aR,7R,7aR)-7-Methoxy-2,2-diMethyl-6-oxo-tetrahydro-4H-furo[3,2-d][1,3]dioxine-4-carbaldehyde serves as a valuable building block for the design and synthesis of new pharmaceutical agents. Its unique structure and functional groups may contribute to the discovery of innovative therapeutics.
Further Research:
Due to the limited understanding of the biological activities and mechanisms of action of (4S,4aR,7R,7aR)-7-Methoxy-2,2-diMethyl-6-oxo-tetrahydro-4H-furo[3,2-d][1,3]dioxine-4-carbaldehyde, ongoing research is essential to uncover its full potential. This may lead to new applications in various industries, including but not limited to pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 270902-65-3 (4R,4aS,7R,7aR)-4-((R)-1,2-dihydroxyethyl)-7-methoxy-2,2-dimethyltetra-hydro-6H-furo[3,2-d][1,3]dioxin-6-one 
• 6605-22-7 3,5:6,7-bis-O-(1-methylethylidene)-α-D-glucoheptonic γ-lactone 
• 1120352-71-7 D-glycero-D-gulco-hepteno-1,4-lactone 
• 89-67-8 α-D-glucoheptonic γ-lactone 
• 136289-11-7 (4R,4aS,7R,7aR)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-7-methoxy-2,2-dimethyl-tetrahydro-6H-furo[3,2-d][1,3]dioxin-6-one 

Relevant academic research and scientific papers

A concise synthesis of bengamide E and analogues via E-selective cross-metathesis olefination

A modular, eight-step synthesis of bengamide E and six analogues from a common chiral pool has been developed. The key step in this approach is a cross-metathesis coupling of various commercial terminal olefins and a common alkene bearing the required ste

Design, Synthesis and Biological Evaluation of Bengamide Analogues as ClpP Activators

To combat multidrug-resistant Gram-positive bacteria, new antimicrobials particularly those with novel mechanism of action are badly needed. Different with conventional antibiotics which are typical inhibitors, small-molecule activators of bacterial ClpP represent a new class of antibiotics. No ClpP activator has been developed for clinical trial. Herein, we conducted a screening on our library of bengamide-like ring-opened analogues and found that L472-2 possesses a low minimum inhibitory concentration (MIC) against S.aureus and shows no activity for ClpP activation in vitro, but it displayed reduced antibacterial activity against S. aureus with clpP deletion. In order to obtain bengamide analogues that activate ClpP in vitro as well as possess antibacterial activity, we perform further structural modifications starting from L472-2. Compound 37 remains the antimicrobial activity and activation of ClpP protein in vitro, which could be viewed as a new chemical scaffold for ClpP activators and worthy of further investigation.

An Expedient Synthesis of LAF389, a Bengamide B Analogue

An optimized, convergent, safe synthesis of LAF389 (9), an anticancer agent analogous to bengamide B, is described. Starting from α-D- glucoheptonic (D-glycero-D-gulo-heptonic acid) γ-lactone (10), the lactone 15 was constructed in five steps. Major impro

Total syntheses of bengamides B and E

Total syntheses of the cytotoxic marine natural products bengamides B and E are described. Both bengamides are prepared via amide coupling of a protected polyhydroxylated lactone intermediate 9 with a suitably substituted aminocaprolactam intermediate. Lactone 9 is prepared in five steps from commercially available α-D-glucoheptonic γ-lactone. The key reactions are a selective deprotection of a 1,2-acetonide in the presence of a 1,3-acetonide and an (E)-selective olefination of an unstable aldehyde using a gem-dichromium reagent. The bengamide B lactam intermediate 10 is prepared in seven steps from commercially available (5R)-5-hydroxy-L-lysine (12). The desired S-configuration at the γ-OH lactam position is established using the Mitsunobu reaction.