251459-19-5

Basic information

• Product Name: 1,2-bis[(2R,5R)-2,5-benzyloxymethylphospholanyl]ethane
• Synonyms: 1,2-bis[(2R,5R)-2,5-benzyloxymethylphospholanyl]ethane
• CAS NO: 251459-19-5
• Molecular Weight: 682.82
• Mol File: 251459-19-5.mol

Chemical Properties

• CAS DataBase Reference: 1,2-bis[(2R,5R)-2,5-benzyloxymethylphospholanyl]ethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-bis[(2R,5R)-2,5-benzyloxymethylphospholanyl]ethane(251459-19-5)
• EPA Substance Registry System: 1,2-bis[(2R,5R)-2,5-benzyloxymethylphospholanyl]ethane(251459-19-5)

Safety Data

• Hazardous Substances Data: 251459-19-5(Hazardous Substances Data)

Upstream product

• 5518-62-7 1,2-diphosphinoethane 
• 251441-73-3 (4S,7S)-4,7-Bis(benzyloxymethyl)-2,2-dioxo[1,3,2]dioxathiepane 
• 127221-55-0 1,6-di-O-benzyl-3,4-dideoxy-D-threo-hexitol 

Relevant articles and documents

Synthesis of chiral 2,5-bis(oxymethyl)-functionalized bis(phospholanes) and their application in Rh- and Ru-catalyzed enantioselective hydrogenations

The synthesis of a series of chiral 2,5-bis(oxymethyl)-substituted bis(phospholanes) 13a-c and 15a,b (BASPHOS) is described, representing functionalized derivatives of the prominent DuPHOS or BPE ligands. D-Mannitol was used as the starting material for these ligands. New bisphospholanes were used as ligands in the enantioselective rhodium(I)-catalyzed hydrogenation of functionalized olefins like unsaturated α- and β-amino acid derivatives, itaconates, and an unsaturated phosphonate. A relevant ruthenium(II) catalyst was used for the reduction of prochiral β-oxo esters. The enantioselectivities, ranging from 8-99% ee, were strongly dependent on the type of the substituent on the oxymethyl group as well on the bridge connecting the phospholane units. Wiley-VCH Verlag GmbH, 2001.

Asymmetric hydrogenation of β-keto esters

Enantiomerically pure β-hydroxy esters are prepared by a process in which β-keto esters are reacted with hydrogen in the presence of catalysts of the formula LRuX2where X is halogen, acetate, allyl, methallyl, 2-phenylallyl, perchlorate, trifluoroacetate, tetrafluoroborate, hexafluoroantimonate, hexafluorophosphate, hexafluoroarsenate or trichloroacetate, L is a bidentate phospholane of the formula I ?where B=a bridging link with 1-5 carbon atoms between the two phosphorus atoms, R1=H, C1-C6-alkyl, aryl, alkylaryl or SiR23, R2=alkyl or aryl, m=0 or 1, R3=H or OR4, and R4=R1, with the proviso that if m=1 then R3=H and if m=0 then R3≠ H.