790661-41-5

Basic information

• Product Name: 2-Thiazolidinethione, 3-acetyl-4-(phenylmethyl)-, (4S)-
• CAS NO: 790661-41-5
• Molecular Formula: C12H13NOS2
• Molecular Weight: 251.373
• Mol File: 790661-41-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Thiazolidinethione, 3-acetyl-4-(phenylmethyl)-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Thiazolidinethione, 3-acetyl-4-(phenylmethyl)-, (4S)-(790661-41-5)
• EPA Substance Registry System: 2-Thiazolidinethione, 3-acetyl-4-(phenylmethyl)-, (4S)-(790661-41-5)

Safety Data

• Hazardous Substances Data: 790661-41-5(Hazardous Substances Data)

Upstream product

• 75-36-5 acetyl chloride 
• 171877-39-7 (S)-4-benzylthiazolidin-2-thione 

Downstream Products

• 1055366-83-0 (R)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-3-hydroxyhexan-1-one 
• 1092564-42-5 (3S)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-3-hydroxybutan-1-one 
• 1445989-90-1 (3S,5R,E)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(tert-butyldimethylsilyloxy)-3-hydroxy-8-methylundeca-8,10-dien-1-one 
• 1445989-91-2 (3R,5R,E)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(tert-butyldimethylsilyloxy)-3-hydroxy-8-methylundeca-8,10-dien-1-one 
• 1445990-01-1 (3S,5S,E)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(tert-butyldimethylsilyloxy)-3-hydroxy-8-methylundeca-8,10-dien-1-one 
• 1445990-02-2 (3R,5S,E)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(tert-butyldimethylsilyloxy)-3-hydroxy-8-methylundeca-8,10-dien-1-one 

Relevant articles and documents

Stereoselective synthesis of maresin 1

Maresin 1 is a potent anti-inflammatory and pro-resolving lipid mediator derived from docosahexaenoic acid. The total synthesis of maresin 1 is achieved in 10 steps and in 7% overall yield. The Evans-Nagao aldol reaction between (2E,4E)-5-bromopenta-2,4-dienal and different chiral auxiliaries is investigated. The reported synthesis is efficient and highly stereoselective, affording multi-milligram quantities of this biologically interesting lipid mediator.

Total synthesis and structural validation of cyclodepsipeptides solonamide A and B

Microorganisms are an attractive source of new natural products with antimicrobial properties, and the marine environment constitutes a prolific resource of bioactive microorganisms. During a global research expedition (Galathea III), two depsipeptides, solonamide A and solonamide B, were isolated from the marine bacterium Photobacterium halotolerance and were found to inhibit virulence gene expression in the serious human pathogen, Staphylococcus aureus. They act by interfering with the agr quorum sensing system and show resemblance to the endogenous S. aureus quorum sensing peptide, autoinducing peptide I (AIP-I). To enable more comprehensive studies, we embarked on the chemical synthesis of solonamides A and B. The key synthetic steps were formation of the (R)-β-hydroxy-fatty-acids by stereo-selective aldol reactions and a cyclative macrolactamization, which proceeded under highly dilute conditions. Thus, the first total syntheses of the solonamides corroborated the originally assigned structures, and by changing the stereochemistry of the auxiliary in the aldol steps we gained access to the natural products as well as their β3-epimers.

Synthesis of the macrocyclic core of (-)-pladienolide B

(Chemical Equation Presented) An efficient synthesis of the macrocyclic core of (-)-pladienolide B is disclosed. The concise route relies on a chiral auxiliary-mediated asymmetric aldol addition and an osmium-catalyzed asymmetric dihydroxylation to install the three oxygenated stereocenters of the macrocycle. This purely reagent-controlled and flexible strategy sets the stage for future analogue syntheses and structure-activity relationship plotting of the appealing anticancer lead structure pladienolide B.