101979-49-1

Basic information

• Product Name: (E,R)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpent-4-en-1-one
• Synonyms: (E,R)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpent-4-en-1-one
• CAS NO: 101979-49-1
• Molecular Weight: 335.491
• Mol File: 101979-49-1.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (E,R)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpent-4-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E,R)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpent-4-en-1-one(101979-49-1)
• EPA Substance Registry System: (E,R)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpent-4-en-1-one(101979-49-1)

Safety Data

• Hazardous Substances Data: 101979-49-1(Hazardous Substances Data)

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 101979-45-7 (S)-3-acetyl-4-isopropyl-1,3-thiazolidine-2-thione 

Downstream Products

• 133321-45-6 C₁₁H₁₄O₂ 
• 153402-93-8 (E)-(2S,4R,5R,7R)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-5-hydroxy-2,4-dimethyl-9-phenyl-7-triisopropylsilanyloxy-non-8-ene-1,3-dione 
• 153402-94-9 (S)-4-Benzyl-3-((E)-(2S,3R,4R,5R,7R)-3,5-dihydroxy-2,4-dimethyl-9-phenyl-7-triisopropylsilanyloxy-non-8-enoyl)-oxazolidin-2-one 
• 153402-95-0 (3S,4R,5S,6R)-4-Hydroxy-3,5-dimethyl-6-((E)-(R)-4-phenyl-2-triisopropylsilanyloxy-but-3-enyl)-tetrahydro-pyran-2-one 
• 153402-90-5 (E)-(R)-5-Phenyl-3-triisopropylsilanyloxy-pent-4-enal 
• 735287-46-4 ethyl (E,R)-5-hydroxy-3-oxo-7-phenylhept-6-enoate 
• 153402-92-7 (E)-(R)-1-((S)-4-Isopropyl-2-thioxo-thiazolidin-3-yl)-5-phenyl-3-triisopropylsilanyloxy-pent-4-en-1-one 

Relevant articles and documents

Stereoselective aldol additions of titanium enolates of N-acetyl-4-isopropyl-thiazolidinethione

The addition of chlorotitanium enolates of N-acetyl isopropyl thiazolidine-2-thione to aldehydes was investigated. The stereoselectivity of the aldol products was controlled by the number of equivalents of base added. The syn aldol product was obtained pr

Enantioselective total synthesis of brevetoxin A: Unified strategy for the B, E, G, and J subunits

Brevetoxin A is a decacyclic ladder toxin that possesses 5-, 6-, 7-, 8-, and 9-membered oxacycles, as well as 22 tetrahedral stereocenters. Herein, we describe a unified approach to the B, E, G, and J rings based upon a ring-closing metathesis strategy from the corresponding dienes. The enolate technologies developed in our laboratory allowed access to the precursor acyclic dienes for the B, E, and G medium-ring ethers. The strategies developed for the syntheses of these four monocycles ultimately provided multigram quantities of each of the rings, supporting our efforts toward the completion of a convergent synthesis of brevetoxin A.

Asymmetric acetate aldol reactions in connection with an enantioselective total synthesis of macrolactin A

Asymmetric aldol-like reactions of cinnamaldehyde, dienal 3 (fragment C7-C12 of macrolactin A), and dienal 4 (fragment C15-C24) with (i) chiral acetylthiazolidinethione-derived enolates, (ii) chiral boron enolates, and (iii) silyl enolates in the presence of chiral titanium-2,2'-dinaphthol complexes are compared. Use of the thiazolidinethiode auxiliary and TiCl4 shows practical advantages; e.g., C5-C12 fragment 7 has been isolated enantiomerically pure in 74% yield. Copyright (C) 1996 Elsevier Science Ltd.