1337951-99-1

Basic information

• Product Name: diethyl hydroxy[5-oxo-2,5-dihydrofuran-2-yl]phenylmethylphosphonate
• Synonyms: diethyl hydroxy[5-oxo-2,5-dihydrofuran-2-yl]phenylmethylphosphonate
• CAS NO: 1337951-99-1
• Molecular Weight: 326.286
• Mol File: 1337951-99-1.mol

Chemical Properties

• CAS DataBase Reference: diethyl hydroxy[5-oxo-2,5-dihydrofuran-2-yl]phenylmethylphosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl hydroxy[5-oxo-2,5-dihydrofuran-2-yl]phenylmethylphosphonate(1337951-99-1)
• EPA Substance Registry System: diethyl hydroxy[5-oxo-2,5-dihydrofuran-2-yl]phenylmethylphosphonate(1337951-99-1)

Safety Data

• Hazardous Substances Data: 1337951-99-1(Hazardous Substances Data)

Upstream product

• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 3277-27-8 diethyl benzoylphosphonate 

Relevant articles and documents

Highly diastereoselective vinylogous Mukaiyama aldol reaction of α-keto phosphonates with 2-(trimethylsilyloxy)furan catalyzed by Cu(OTf)2

The diastereospecific formation of δ-hydroxyalkylbutenolide phosphonate has been achieved via a vinylogous Mukaiyama aldol reaction. The reaction was performed using α-ketophosphonate 1 and 2-(trimethylsilyloxy) furan 2 mediated by Cu(OTf)2 and 2,2,2-trifluoroethanol as additive in CH2Cl2. The reaction proceeds rapidly and affords the corresponding 5-(hydroxy(aryl)methyl) furan-2(5H)-one phosphonates 3 in high yields with good to excellent diastereoselectivities (d.r. up to >99:1). 5-(Hydroxy(alkyl)methyl)furan-2(5H)-one phosphonates could also be obtained with good diastereoselectivities.

Catalytic, asymmetric synthesis of phosphonic γ-(hydroxyalkyl) butenolides with contiguous quaternary and tertiary stereogenic centers

A procedure that enables high yielding access to phosphonic γ-(hydroxyalkyl)butenolides with excellent regio-, diastereo- and enantiocontrol is reported. The simultaneous construction of up to two adjacent quaternary stereogenic centers by a catalytic asymmetric vinylogous Mukaiyama aldol reaction unites biologically and medicinally relevant entities, namely α-hydroxy phosphonates and γ-(hydroxyalkyl)butenolides. This is achieved by utilizing a readily available chiral copper-sulfoximine catalyst showing a broad functional group tolerance for both the electrophilic and nucleophilic reactants. A discussion about potential factors affecting the observed level of enantioselectivity, which stems from the enantiopure sulfoximine ligand, is also included. Best of two worlds: A chiral copper-sulfoximine catalyst unites biologically relevant α-hydroxy phosphonates and γ-(hydroxyalkyl) butenolides into one structural motif with regio-, diastereo- and enantioselectivity up to the limits of detection (see scheme; Tf=trifluoromethanesulfonyl, TMS=trimethylsilyl). Copyright