126983-40-2

Basic information

• Product Name: (1S,2R,3R,4R)-3-Benzyloxy-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid benzyl ester
• CAS NO: 126983-40-2
• Molecular Weight: 334.415
• Mol File: 126983-40-2.mol

Chemical Properties

• CAS DataBase Reference: (1S,2R,3R,4R)-3-Benzyloxy-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R,3R,4R)-3-Benzyloxy-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid benzyl ester(126983-40-2)
• EPA Substance Registry System: (1S,2R,3R,4R)-3-Benzyloxy-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid benzyl ester(126983-40-2)

Safety Data

• Hazardous Substances Data: 126983-40-2(Hazardous Substances Data)

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 127658-14-4 (1S,2S,3R,4R)-3-Bromo-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 
• 20194-18-7 sodium phenyl-methanolate 
• 126983-28-6 (E)-3-bromoacrylate of (R)-pantolactone 

Downstream Products

• 127658-18-8 (3aS,4S,5S,6aR)-4-Benzyloxy-1-oxo-hexahydro-cyclopenta[c]furan-5-carboxylic acid 
• 127658-17-7 Acetic acid (1S,2S,3R,4R)-3-benzyloxy-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 
• 127658-19-9 (3aS,4R,6aR)-4-Benzyloxy-hexahydro-cyclopenta[c]furan-1-one 
• 127708-92-3 ((1S,2R,3S,4R)-3-Benzyloxy-bicyclo[2.2.1]hept-5-en-2-yl)-methanol 
• 127658-16-6 ((1S,2S,3R,4R)-3-Benzyloxy-bicyclo[2.2.1]hept-5-en-2-yl)-methanol 
• 127708-93-4 ((1S,2R,3R,4R)-3-Benzyloxy-bicyclo[2.2.1]hept-5-en-2-yl)-methanol 

Relevant articles and documents

N-SUBSTITUTED HYDROXYSUCCINIMIDES FROM (S)-MALIC ACID AS NEW REAGENTS FOR ASYMMETRIC DIELS-ALDER ADDITION TO ENOATES

(S)-N-Methyl-2-hydroxysuccinimide, easily available from natural (S)-malic acid, supplements the previously introduced (R)-pantolactone as chiral auxiliary for asymmetric Diels-Alder reactions of enoates, but yields products of opposite configuration.Practical large-scale preparations of enantiomer pairs of synthetically important Diels-Alder adducts, including adducts from crotonates, are described.

ASYMMETRIC DIELS-ALDER REACTIONS: EPC-SYNTHESIS OF A STABLE SARKOMYCIN PRECURSOR (CYCLOSARKOMYCIN)

The first synthesis of enantiomerically pure cyclosarkomycin, a stable, crystaline precursor of the antitumor agent sarkomycin is reported.Key steps are an asymmetric Diels-Alder reaction of the (E)-3-bromoacrylate of (R)-pantolactone and introduction of oxygen funtionality via elimination/β-addition.The synthesis of cyclosarkomycin was accomplished in 9 steps in 17 percent overall yield.