100017-03-6

Basic information

• Product Name: 3(S(R))-<5(R(S))-methyl-2(S(R))-tetrahydrofuryl>-3-(phenylselenyl)-2,5-pyrrolidinedione
• Synonyms: 3(S(R))-<5(R(S))-methyl-2(S(R))-tetrahydrofuryl>-3-(phenylselenyl)-2,5-pyrrolidinedione
• CAS NO: 100017-03-6
• Molecular Weight: 338.265
• Mol File: 100017-03-6.mol

Chemical Properties

• CAS DataBase Reference: 3(S(R))-<5(R(S))-methyl-2(S(R))-tetrahydrofuryl>-3-(phenylselenyl)-2,5-pyrrolidinedione(CAS DataBase Reference)
• NIST Chemistry Reference: 3(S(R))-<5(R(S))-methyl-2(S(R))-tetrahydrofuryl>-3-(phenylselenyl)-2,5-pyrrolidinedione(100017-03-6)
• EPA Substance Registry System: 3(S(R))-<5(R(S))-methyl-2(S(R))-tetrahydrofuryl>-3-(phenylselenyl)-2,5-pyrrolidinedione(100017-03-6)

Safety Data

• Hazardous Substances Data: 100017-03-6(Hazardous Substances Data)

Upstream product

• 18545-25-0 5-methyl-tetrahydro-furan-2-ol 
• 5707-04-0 Phenylselenyl chloride 
• 92013-82-6 3(E)-(4-hydroxypentylidene)-2,5-pyrrolidinedione 

Relevant articles and documents

Two Total Syntheses of Showdomycin and Related Studies

After a series of model reactions, D-ribose (2) was reacted with 3-(triphenylphosphoranylidene)-2,5-pyrrolidinedione (8a) in THF at reflux to produce 3(E)-2(S),3(S),4(R),5-tetrahydroxy-1-pentylidene)-2,5-pyrrolidinedione (35) (75 percent).Subsequent cyclization of 35 using phenylselenyl chloride followed by hydrogen peroxide gave showdomycin (1) (13 percent) and epi-showdomycin (36) (41 percent).Using a similar strategy 2,3-O-isopropylidene-D-ribose (37b) was reacted sequentially with 1-(triphenylmethyl)-3-(triphenylphosphoranylidene)-2,5-pyrrolidinedione (8b), phenylselenyl chloride, hydrogen peroxide, and trifluoroacetic acid to give (1) (3 percent overall).