952057-96-4

Basic information

• Product Name: (Z)-3-deoxy-3-C-[(ethoxycarbonyl)methylene]-1,2-O-isopropylidene-5-O-triphenylmethyl-α-D-erythro-pentose
• Synonyms: (Z)-3-deoxy-3-C-[(ethoxycarbonyl)methylene]-1,2-O-isopropylidene-5-O-triphenylmethyl-α-D-erythro-pentose
• CAS NO: 952057-96-4
• Molecular Weight: 500.591
• Mol File: 952057-96-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (Z)-3-deoxy-3-C-[(ethoxycarbonyl)methylene]-1,2-O-isopropylidene-5-O-triphenylmethyl-α-D-erythro-pentose(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-3-deoxy-3-C-[(ethoxycarbonyl)methylene]-1,2-O-isopropylidene-5-O-triphenylmethyl-α-D-erythro-pentose(952057-96-4)
• EPA Substance Registry System: (Z)-3-deoxy-3-C-[(ethoxycarbonyl)methylene]-1,2-O-isopropylidene-5-O-triphenylmethyl-α-D-erythro-pentose(952057-96-4)

Safety Data

• Hazardous Substances Data: 952057-96-4(Hazardous Substances Data)

Upstream product

• 87-72-9 D-Xylose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 20590-53-8 1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 20590-54-9 1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose 
• 76-83-5 trityl chloride 

Downstream Products

• 1030604-48-8 3-phenyl-2H-furo[2,3-c]pyran-2-one 
• 857054-03-6 2H-furo[2,3-c]pyran-2-one 
• 857054-02-5 3-methyl-2H-furo[2,3-c]pyran-2-one 

Relevant articles and documents

Discovery of cytochrome bc1 complex inhibitors inspired by the natural product karrikinolide

The cytochrome bc1 complex (cyt bc1 or complex III) is a promising target of numerous antibiotics and fungicides. With an aim to indentify new lead structures for the bc1 complex, a series of novel inhibitors were discovered from the natural product karrikinolide for the first time. Extensive screening results suggested variable inhibitory activities of these compounds against succinate-cytochrome reductase [SCR, a mixture of respiratory complex II (SQR) and complex III (the bc1 complex)], implying the essential role of a 4-substituted phenyl group for the high potency. Exceptionally, compound 12g showed excellent inhibition potency having an IC50 value in the sub-micromolar range, demonstrating its higher potency than the commercial control amisulbrom by over two orders of magnitude. Further experiments inferred that these newly prepared compounds mainly target the bc1 complex. Seemingly, this work has presented a new lead scaffold for further development of bc1 complex inhibitors.

Synthesis of the germination stimulant 3-methyl-2H-furo[2,3-c]pyran-2-one and analogous compounds from carbohydrates

An efficacious synthetic route to the recently identified, potent germination stimulant 3-methyl-2H-furo[2,3-c]pyran-2-one and analogous compounds, using carbohydrate substrates, is described. D-Xylose and D-glucuronic acid γ-lactone were used in the preparation of the parent heterocycle and its 5-methoxycarbonyl analogue, respectively. These compounds were elaborated using various methods to furnish the natural product and a suite of its analogues. The germination stimulant was thus prepared on a multi-gram scale in nine steps from inexpensive, commercially available 1,2-O-isopropylidene-D-xylofuranose in an overall yield of 30 %, vastly improving upon the only method published to date. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.