183013-60-7

Basic information

• Product Name: 2H-Pyran-2-carboxylicacid,3,4-dihydro-4-oxo-,methylester,(2R)-(9CI)
• Synonyms: 2H-Pyran-2-carboxylicacid,3,4-dihydro-4-oxo-,methylester,(2R)-(9CI)
• CAS NO: 183013-60-7
• Molecular Formula: C7H8O4
• Molecular Weight: 0
• Product Categories: CARBOXYLICESTER
• Mol File: 183013-60-7.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2H-Pyran-2-carboxylicacid,3,4-dihydro-4-oxo-,methylester,(2R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Pyran-2-carboxylicacid,3,4-dihydro-4-oxo-,methylester,(2R)-(9CI)(183013-60-7)
• EPA Substance Registry System: 2H-Pyran-2-carboxylicacid,3,4-dihydro-4-oxo-,methylester,(2R)-(9CI)(183013-60-7)

Safety Data

• Hazardous Substances Data: 183013-60-7(Hazardous Substances Data)

Upstream product

• 922-68-9 Methyl glyoxylate 
• 71735-01-8 (E)-3-(tert-butyldimethylsilyloxy)-1-methoxy-1,3-butadiene 
• 59414-23-2 1-methoxy-3-<(trimethylsilyl)oxy>01,3-butadiene 
• 54125-02-9 danishefsky's diene 
• 18107-18-1 diazomethyl-trimethyl-silane 

Relevant articles and documents

Asymmetric hetero-diels-alder reaction of danishefsky's dienes with α-carbonyl esters catalyzed by an indium(III)-PyBox complex

An efficient catalytic enantioselective hetero-Diels-Alder reaction of Danishefsky's dienes with α-carbonyl esters using a chiral In(III)-pybox complex has been demonstrated. This protocol offers several advantages, including mild reaction conditions, relatively low catalyst loading, and good to excellent enantioselectivities. Furthermore, the absolute configurations of the new alkynyl-containing products were determined by CD spectra in combination with TD-DFT calculations.

Asymmetric hetero Diels-Alder reaction of Danishefsky's dienes and glyoxylates with chiral bis(oxazolinyl)phenylrhodium(III) aqua complexes, and its mechanistic studies

Asymmetric hetero Diels-Alder reaction of Danishefsky's dienes with glyoxylates is catalyzed in high enantioselectivity and cis (endo)-diastereoselectivity by chiral (Phebox)RhCl2(H2O) complexes [Phebox=2,6-bis(oxazolinyl)phenyl], via the concerted [4+2] mechanism with perpendicular conformation of two carbonyl moieties of glyoxylates. Dibromide and difluoride complexes were newly synthesized and found to exhibit a slightly higher enantioselectivity of the hetero Diels-Alder products than the parent dichloride complex (Cl: 80% ee, Br: 82% ee, F: 84% ee).

Asymmetric hetero Diels-Alder reactions of Danishefsky's diene and glyoxylate esters catalyzed by chiral bisoxazoline derived catalysts

Asymmetric hetero Diels-Alder reactions of Danishefsky's diene and glyoxylate esters catalyzed by bis(oxazoline)-metal complex afforded the corresponding aldol adduct which upon treatment with trifluoroacetic acid furnished the hetero Diels-Alder product in 72% enantiomeric excess and 70% isolated yield.